DK145295B - Fremgangsmaade til fremstilling af aromatiske urethaner - Google Patents
Fremgangsmaade til fremstilling af aromatiske urethaner Download PDFInfo
- Publication number
- DK145295B DK145295B DK164477AA DK164477A DK145295B DK 145295 B DK145295 B DK 145295B DK 164477A A DK164477A A DK 164477AA DK 164477 A DK164477 A DK 164477A DK 145295 B DK145295 B DK 145295B
- Authority
- DK
- Denmark
- Prior art keywords
- aromatic
- yield
- urants
- procedure
- manufacture
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 16
- 229960001413 acetanilide Drugs 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- -1 aromatic urethanes Chemical class 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 101100082060 Xenopus laevis pou5f1.1 gene Proteins 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SUDHEDJJFGYYPL-UHFFFAOYSA-N ethyl n,n-dimethylcarbamate Chemical compound CCOC(=O)N(C)C SUDHEDJJFGYYPL-UHFFFAOYSA-N 0.000 description 1
- WXDDBYFBIIAYSM-UHFFFAOYSA-N ethyl n-(2-phenylethyl)carbamate Chemical compound CCOC(=O)NCCC1=CC=CC=C1 WXDDBYFBIIAYSM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
fåf (19) DANMARK \Ra>
|jf ( 2) FREMLÆGGELSESSKRIFT (11) 145295B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENET
(21) Ansøgning nr. 1644/77 (51) IntCI.3 C 07 C 125/065 (22) Indleveringsdag 15. apr. 1977 C 07 C 125/073 (24) Løbedag 13. apr. 1977 (41) Aim. tilgængelig 15. 0kt. 1977 (44) Fremlagt 25. okt. 1982 (86) International ansøgning nr. -(86) International indleveringsdag ..
(85) Videreførelsesdag -(62) Stamansøgning nr. .
(30) Prioritet 14. apr. 1976, 22299/76, IT
(71) Ansøger ANIC S.P.A., Palermo, IT.
(72) Opfinder jjg0 Romano, IT: Renato Tes el, IT.
(74) Fuldmægtig internationalt Patent-Bureau.
(54) Fremgangsmåde til fremstilling af aromatiske urethaner.
Den foreliggende opfindelse angår en fremgangsmåde til fremstilling af aromatiske urethaner med formlen
Ar-NH-l-OR
eller med formlen
ROCONH-Ar'-NHCOOR
m hvori Ar og Ar' er aromatiske grupper afledt af phenyl, biphenyl, LO naphthyl eller diphenylmethan, eventuelt substitueret
CD
^ med alkyl-, alkoxy- eller arylgrupper, og R betegner alkyl.
LO Det er kendt, at sådanne forbindelser kan fremstilles ud fra J· t—· de respektive aminer og chlorformiater, eller ud fra isocyanater og *
O
145295 2 alkoholer, ved fremgangsmåder, som involverer anvendelsen af yderst toksiske reagenser.
Det er ligeledes kendt, at produkter af denne klasse finder anvendelse på områderne ukrudtsbekæmpelsesmidler og pesticider.
Det har for nyligt vist sig, at sådanne forbindelser kan fremstilles ud fra aminer og dialkylcarbonater i nærværelse af Lewis-syrer (US patentskrift nr. 3.763.217), men ved reaktionen dannes der foruden de ventede produkter urinstoffer og alkylaminer, således at selektiviteten for de ønskede produkter kun andrager 20%.
Det har nu vist sig, at de angivne aromatiske urethaner kan opnås med en praktisk taget total selektivitet og en omdannelse på over 90%, når man på kendt måde går ud fra dialkylcarbonater, hvis alkylgrupper svarer til R ovenfor, eventuelt i nærværelse af en Lewis-syre, og ifølge opfindelsen bringer dialkylcarbonatet til at reagere med et N-acylderivat' af en amin med formlen
Ar-NH-Ac eller med formlen
Ac-NH-Ar'-NH-Ac hvori Ac er en acetyl- eller propionylgruppe.
Omsætningen finder fortrinsvis sted i nærværelse af Lewis-syrer og mere specielt halogenider, alkoholater og phenater af aluminium og titan.
Under reaktionens fremadskriden dannes aromatiske urethaner og estere af den til N-acylderivatet svarende syre og de til grund for alkylcarbonaterne liggende alkoholer. Reaktionen som sådan udføres ved en temperatur i området 50 - 200°C og under et •tryk mellem 0,1 og 20 abs. atmosfærer.
De efterfølgende eksempler forklarer fremgangsmåden ifølge opfindelsen nærmere.
Eksempel 1 I en 250 ml kolbe, der afsluttes af en kolonne med 20 bunde og en væske-fraskillende top, omsættes 132 g diethylcarbonat (DEC), 25,5 g acetanilid og 4,8 g titantetraphenat.
Efter 1 times forløb ved 130°C er der opnået 16 g (udbytte 96%) ethylacetat som topdestillat.
Udbyttet af phenylethylurethan er over 90%.
Omsætningen af acetanilid er 100%. Der blev ikke påvist noget diphenylurinstof.
145295 3
Eksempel 2 I det i eksempel 1 omhandlede apparat blev der indført 100,5 g dimethylcarbonat (DMC) og 25,1 g acetanilid med 4,8 g titantetraphe-nat.
Efter 2 timers forløb ved 110°C blev der som topdestillat opnået 13,3 g methylacetat (udbytte 96,2%) .
Udbyttet af phenylmethylurethan var over 90%.
Omsætningen af acetanilid var 100%.
Eksempel 3
En 500 ml kolbe blev forsynet med 19,5 g N,Ν'-bis-acetyl-2,4-tolylendiamin og 300 g DMC med 2,4 g Ti(OPh)4·
Efter 5 timers forløb ved 120°C var der opnået 13,9 g methylacetat som topdestillat (udbytte 100%) og 22 g bis-methylurethan af tolylendiamin (udbytte 99%).
Eksempel 4 I det i eksempel 1 omhandlede apparatur blev der indført 10 g acetanilid, 80 g DMC og 1,27 g titantetramethylat.
Efter 4 timers forløb ved 120°C blev der som topdestillat af-destilleret 7,5 g methylacetat (udbytte 72%) med 80%'s omsætning af acetanilid.
Der blev opnået ca. 10 g phenylmethylurethan med et udbytte på ca. 70% og en selektivitet på ca. 70%.
Eksempel 5 I det i eksempel 1 omhandlede apparatur blev der indført 20 g acetanilid, 80 g DMC og 1,51 g Al(O-isopropyl)3.
Efter 4 timers forløb ved 120°C blev der som topdestillat opnået 13,1 methylacetat og 18,4 g phenylmethylurethan (udbytte 82%) med en acetanilidomsætning på 90%.
Eksempel 6
Det i eksempel 1 omhandlede apparat blev tilført 23 g propion-anilid, 85 g DMC og 1,5 g TiCl^.
Efter 4 timers forløb blev der som topdestillat opnået methyl-propionat i 100%'s udbytte, med en total omsætning af propionaldehy-det og et udbytte på ca. 92% phenylmethylurethan.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22299/76A IT1064762B (it) | 1976-04-14 | 1976-04-14 | Processo per la preparazione di ureiani aromatici |
| IT2229976 | 1976-04-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK164477A DK164477A (da) | 1977-10-15 |
| DK145295B true DK145295B (da) | 1982-10-25 |
| DK145295C DK145295C (da) | 1983-04-18 |
Family
ID=11194364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK164477A DK145295C (da) | 1976-04-14 | 1977-04-13 | Fremgangsmaade til fremstilling af aromatiske urethaner |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4100351A (da) |
| JP (1) | JPS52125147A (da) |
| BE (1) | BE853606A (da) |
| BG (1) | BG30770A3 (da) |
| CS (1) | CS191338B2 (da) |
| DD (1) | DD129647A5 (da) |
| DE (1) | DE2716540C3 (da) |
| DK (1) | DK145295C (da) |
| FR (1) | FR2348195A1 (da) |
| GB (1) | GB1519131A (da) |
| HU (1) | HU174664B (da) |
| IT (1) | IT1064762B (da) |
| NL (1) | NL179374C (da) |
| NO (1) | NO149310C (da) |
| PL (1) | PL106065B1 (da) |
| RO (1) | RO72531A (da) |
| SE (1) | SE427838B (da) |
| SU (1) | SU860693A1 (da) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK151499B (da) * | 1977-09-28 | 1987-12-07 | Stanadyne Inc | Fluidumventil med et cylindrisk muffeorgan, som indeholder en frem- og tilbagebevaegelig ventilstyredel til styring af en fluidumstroem gennem ventilen |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258201A (en) * | 1979-01-29 | 1981-03-24 | Halcon Research And Development Corp. | Process for the manufacture of carbamates |
| US4266070A (en) * | 1979-05-25 | 1981-05-05 | Halcon Research And Development Corp. | Catalytic process for the manufacture of urethanes |
| US4260781A (en) * | 1979-05-25 | 1981-04-07 | Halcon Research And Development Corp. | Process for the manufacture of carbamates |
| DE2942503A1 (de) * | 1979-10-20 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von aromatischen di- und/oder polyisocyanaten |
| US4258200A (en) * | 1980-03-11 | 1981-03-24 | Air Products And Chemicals, Inc. | Production of carboxylic acid amides and carbamates using cobalt catalysts |
| DE3035354A1 (de) * | 1980-09-19 | 1982-04-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n,o-disubstituierten urethanen und ihre verwendung als ausgangsmaterial zur herstellung von organischen isocyanaten |
| DE3036966A1 (de) * | 1980-10-01 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n,o-disubstituierten urethanen und ihre verwendung als ausgangsmaterial zur herstellung von organischen isocyanaten |
| US4550188A (en) * | 1984-06-27 | 1985-10-29 | The Dow Chemical Company | Preparation of carbamates |
| US4567287A (en) * | 1984-08-08 | 1986-01-28 | The Upjohn Co. | Preparation of carbamates from organic carbonates and aromatic ureas |
| EP0297610B1 (en) * | 1987-07-02 | 1991-03-13 | Warner-Lambert Company | N-[(2,6-disubstituted)phenyl]-urea and carbamate inhibitors of acyl-CoA:cholesterol acyl-transferase |
| CA1338868C (en) * | 1988-04-25 | 1997-01-21 | Theophilus F. Leapheart | Process for the production of cis-hydroxy trans-phenoxycyclopentylamines |
| US5166414A (en) * | 1989-12-28 | 1992-11-24 | Mitsubishi Gas Chemical Company, Inc. | Process for producing isocyanate compound |
| JP2918012B2 (ja) * | 1993-02-03 | 1999-07-12 | 三菱瓦斯化学株式会社 | ウレタン化合物の製造方法 |
| JPH06239289A (ja) * | 1993-02-16 | 1994-08-30 | Mitsubishi Heavy Ind Ltd | プリント配線式船体構造 |
| US6781010B1 (en) * | 2000-09-19 | 2004-08-24 | Lyondell Chemical Company | Non-phosgene route to the manufacture of organic isocyanates |
| CN101130508B (zh) * | 2006-08-22 | 2011-05-04 | 中国科学院过程工程研究所 | 一种常压条件下合成苯氨基甲酸酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3938986A (en) * | 1969-03-17 | 1976-02-17 | Ppg Industries, Inc. | Herbicide |
| US3763217A (en) * | 1970-12-03 | 1973-10-02 | Halcon International Inc | Preparation of carbamates |
| GB1337877A (en) * | 1971-05-24 | 1973-11-21 | Ici Australia Ltd | Process for the preparation of n-acyl and n-aroyl carbamates |
| GB1494340A (en) * | 1974-12-03 | 1977-12-07 | Wyeth John & Brother Ltd | Process for preparation of substituted n-phenylcarbamate esters |
-
1976
- 1976-04-14 IT IT22299/76A patent/IT1064762B/it active
-
1977
- 1977-03-24 US US05/781,065 patent/US4100351A/en not_active Expired - Lifetime
- 1977-03-28 GB GB12986/77A patent/GB1519131A/en not_active Expired
- 1977-04-04 RO RO7789902A patent/RO72531A/ro unknown
- 1977-04-04 BG BG035904A patent/BG30770A3/xx unknown
- 1977-04-08 SU SU772469148A patent/SU860693A1/ru active
- 1977-04-12 DD DD7700198360A patent/DD129647A5/xx unknown
- 1977-04-12 CS CS772388A patent/CS191338B2/cs unknown
- 1977-04-13 NO NO771277A patent/NO149310C/no unknown
- 1977-04-13 FR FR7711138A patent/FR2348195A1/fr active Granted
- 1977-04-13 HU HU77AI270A patent/HU174664B/hu unknown
- 1977-04-13 JP JP4160677A patent/JPS52125147A/ja active Pending
- 1977-04-13 DK DK164477A patent/DK145295C/da not_active IP Right Cessation
- 1977-04-13 SE SE7704247A patent/SE427838B/xx not_active IP Right Cessation
- 1977-04-14 NL NLAANVRAGE7704117,A patent/NL179374C/xx not_active IP Right Cessation
- 1977-04-14 BE BE176725A patent/BE853606A/xx not_active IP Right Cessation
- 1977-04-14 DE DE2716540A patent/DE2716540C3/de not_active Expired
- 1977-04-14 PL PL1977197403A patent/PL106065B1/pl unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK151499B (da) * | 1977-09-28 | 1987-12-07 | Stanadyne Inc | Fluidumventil med et cylindrisk muffeorgan, som indeholder en frem- og tilbagebevaegelig ventilstyredel til styring af en fluidumstroem gennem ventilen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7704117A (nl) | 1977-10-18 |
| NO149310B (no) | 1983-12-19 |
| SE7704247L (sv) | 1977-10-15 |
| SE427838B (sv) | 1983-05-09 |
| DE2716540B2 (de) | 1979-03-15 |
| JPS52125147A (en) | 1977-10-20 |
| CS191338B2 (en) | 1979-06-29 |
| PL106065B1 (pl) | 1979-11-30 |
| NL179374B (nl) | 1986-04-01 |
| DK145295C (da) | 1983-04-18 |
| FR2348195A1 (fr) | 1977-11-10 |
| HU174664B (hu) | 1980-03-28 |
| NO771277L (no) | 1977-10-17 |
| BG30770A3 (en) | 1981-08-14 |
| NO149310C (no) | 1984-03-28 |
| IT1064762B (it) | 1985-02-25 |
| DK164477A (da) | 1977-10-15 |
| RO72531A (ro) | 1981-06-30 |
| SU860693A1 (ru) | 1981-08-30 |
| DE2716540A1 (de) | 1977-10-20 |
| NL179374C (nl) | 1986-09-01 |
| FR2348195B1 (da) | 1980-01-18 |
| DD129647A5 (de) | 1978-02-01 |
| DE2716540C3 (de) | 1979-11-22 |
| US4100351A (en) | 1978-07-11 |
| BE853606A (fr) | 1977-10-14 |
| GB1519131A (en) | 1978-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |