KR830006170A - 메타-클로로 아닐린의 선택적 제조방법 - Google Patents
메타-클로로 아닐린의 선택적 제조방법 Download PDFInfo
- Publication number
- KR830006170A KR830006170A KR1019810002798A KR810002798A KR830006170A KR 830006170 A KR830006170 A KR 830006170A KR 1019810002798 A KR1019810002798 A KR 1019810002798A KR 810002798 A KR810002798 A KR 810002798A KR 830006170 A KR830006170 A KR 830006170A
- Authority
- KR
- South Korea
- Prior art keywords
- chlorine
- reaction
- carried out
- atom
- hydrogen
- Prior art date
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- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 17
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 238000006243 chemical reaction Methods 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 239000002841 Lewis acid Substances 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000007517 lewis acids Chemical class 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 150000001555 benzenes Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052787 antimony Inorganic materials 0.000 claims 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 229910052793 cadmium Inorganic materials 0.000 claims 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- 229940045803 cuprous chloride Drugs 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/46—Aniline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (19)
- 하기식 (Ⅰ)의 질소-함유 및 염소-함유 벤젠 유도체를 주기율표 Ⅶ족의 귀금속의 존재하에서, 액상에서, 열 및 압력을 가하면서접촉 수소 첨가 반응 시킴을 특징으로 하는, 특히 반응은 촉매로서 적어도 하나의 루이스산의 촉매의 양이 존재하에서 수행시킴을 특징으로 하는 메타-위치가 염소로 치환된 아닐린의 제조방법.식중 Y는 수소원자 또는 산소원자이고, X'밑 X"는 같거나 다르고, 각각은 염소원자 또는 임의로 치환된 알킬, 아릴, 아랄킬, 알콕시 또는 아랄콕시 라디칼이고, X' 및 X"의 적어도 하나는 염소원자이고, 더욱이 X' 및 X"의 하나는 수소일 수도 있고, R',R" 및 R'"는 같거나 다르고, 각각은 염소원자 또는 임의로 치환된 알킬, 아랄킬, 알콕시, 또는 아릴옥시라디칼이고, 셋중의 적어도 하나는 염소원자이고, R',R" 또는 R'"의 최대한 둘은 수소원자일 수 있다.
- 루이스산이 붕소, 알루미늄, 갈륨, 주석, 인, 비소, 안티몬, 비스무드, 티타늄, 지르코늄, 몰리브덴, 망간, 철, 코발트, 니켈, 구리, 아연 및 카드뮴 중에서 택한 원소의 할라이드임을 특징으로 하는 특허청구범위 제1항 기재에 의한 방법
- 반응을 염화 및 브롬화 알루미늄, 염화 제1스탄 및 제2스탄, 염화 제2철, 염화 및 요오드화 아연, 염화제1구리 및 염화니켈 중에서 택한 화합물의 촉매의 존재하에 수행 시킴을 특징으로 하는 특허청구의 범위 제 2항 기재에 의한 방법.
- 루이스산 대 초기 질소-함유 및 염소-함유 벤젠 유도체의 물 비율이 0.0001∼1임을 특징으로 하는 특허청구의 범위 제1∼제3항 기재중의 방법.
- 루이스산대 초기 질소-함유 및 염소-함유 벤젠 유도체의 물 비율이 0.01∼0.5임을 특징으로 하는 특허청구범위 제4항 기재에 의한 방법
- 반응을 용융된 원료중에서 수행시킴을 특징으로 하는 특허청구의범위 제1∼제5항 기재중의 방법.
- 반응을 유기용매중의 용액에서 수행시킴을 특징으로 하는 특허청구의 범위 제1∼제5항 기재중의 방법.
- R',R",R'",X' 및 X"가 같거나 다르고, 수소원자 또는 염소원자임을 특징으로 하는 특허청구의 범위 제1∼제7항 기재중의 방법.
- X'및 X"가 염소 원자임을 특징으로 하는 특허청구의 범위 제1∼제8항 기재에 의한 임의로 치환된 메타-디클로로아닐린의 제조방법.
- 2개의 라디칼 X' 및 X"중의 단지 1개가 염소원자임을 특징으로 하는 특허청구의 범위 제1∼제8항기재에 의한 임의로 치환된 메타-모노클로로아닐린의 제조방법.
- Y는 수소 또는 산소원자이고, X' 및 X"는 염소원자이고, R',R" 및 R'"는 적어도 하나가 염소원자인 수소원자 또는 염소원자를 특징으로 하는 특허청구의 범위 제1∼제11항 기재에 의한 방법.
- 반응 매질이 촉매가 귀금속인 것을 제외하고 단지 액상을 함유하는 것을 특징으로 하는 특허청구의 범위 제1∼제11항 기재에 의한 방법.
- 반응을 3바 이하에 압력해서 수행시키는 특징으로 하는 특허청구의 범위 제1∼11항 기재에 의한 방법.
- 반응을 대기압에서 수행시키는 특징으로 하는 특허청구의 범위 제13항 기재에 의한 방법.
- 전압이 3∼100바 임을 특징으로 하는 특허청구의 범위제1∼제12항 기재에 의한 방법.
- 전압이 5∼20바임을 특징으로 하는 특허청구의 범위 제15항 기재에 의한 방법.
- 온도가 90∼300℃, 바람직하기로는 110∼200℃임을 특징으로 하는 특허청구의 범위 제1∼제16항 기재에 의한 방법.
- 촉매가 팔라듐임을 특징으로 하는 특허청구의 범위 제1∼제17항 기재에 의한 방법.
- 귀금속 대 식(Ⅰ)화합물의무게비가 0.01∼10%, 바람직하기로는 0.1∼5%임을 특징으로 하는 특허청구의 범위 제1∼제18항 기재에 의한 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8017324A FR2487823A1 (fr) | 1980-08-01 | 1980-08-01 | Procede de preparation selective d'anilines metachlorees |
FR80/17324 | 1980-08-01 | ||
FR8020979A FR2491059A2 (fr) | 1980-09-26 | 1980-09-26 | Procede de preparation selective d'anilines metachlorees |
FR80/20979 | 1980-09-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830006170A true KR830006170A (ko) | 1983-09-17 |
KR850000148B1 KR850000148B1 (ko) | 1985-02-28 |
Family
ID=26221937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810002798A KR850000148B1 (ko) | 1980-08-01 | 1981-08-01 | 메타-클로로아닐린유도체의 제조방법 |
Country Status (13)
Country | Link |
---|---|
US (1) | US4418213A (ko) |
EP (1) | EP0045709B1 (ko) |
KR (1) | KR850000148B1 (ko) |
BR (1) | BR8104979A (ko) |
CA (1) | CA1211470A (ko) |
DD (1) | DD201673A5 (ko) |
DE (1) | DE3166482D1 (ko) |
DK (1) | DK342981A (ko) |
ES (1) | ES8306092A1 (ko) |
HU (1) | HU187348B (ko) |
IE (1) | IE51457B1 (ko) |
IL (1) | IL63297A (ko) |
SU (1) | SU1176830A3 (ko) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2532305A1 (fr) * | 1982-08-24 | 1984-03-02 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
USRE34745E (en) * | 1986-10-30 | 1994-09-27 | The Dow Chemical Company | High purity process for the preparation of 4,6-diamino-1,3-benzenediol |
US5001279A (en) * | 1989-11-17 | 1991-03-19 | The Dow Chemical Company | Aqueous synthesis of 2-halo-4,6-dinitroresorcinol and 4,6-diaminoresorcinol |
US5051030A (en) * | 1990-06-05 | 1991-09-24 | Roy F. Weston, Inc. | Chemical detoxification process for treatment of soils contaminated with halogenated organic compounds |
JPH0565250A (ja) * | 1991-01-28 | 1993-03-19 | Ishihara Sangyo Kaisha Ltd | 3,5−ジフルオロアニリンの製造方法 |
US5089653A (en) * | 1991-04-04 | 1992-02-18 | Dow Elanco | Process for the selective reduction of the 4-halogen in 2,4-dihaloanilines |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU517576A1 (ru) * | 1971-05-24 | 1976-06-15 | Предприятие П/Я А-7797 | Способ получени смешанных галоидароматических углеводородов |
DE2503187C3 (de) * | 1975-01-27 | 1979-05-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung durch Chlor meta-substituierte Aniline |
FR2449075A1 (fr) * | 1979-02-15 | 1980-09-12 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
FR2449076A2 (fr) * | 1979-02-15 | 1980-09-12 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
-
1981
- 1981-07-13 IL IL63297A patent/IL63297A/xx unknown
- 1981-07-14 US US06/283,151 patent/US4418213A/en not_active Expired - Fee Related
- 1981-07-30 CA CA000382858A patent/CA1211470A/en not_active Expired
- 1981-07-30 DE DE8181420115T patent/DE3166482D1/de not_active Expired
- 1981-07-30 IE IE1738/81A patent/IE51457B1/en unknown
- 1981-07-30 EP EP81420115A patent/EP0045709B1/fr not_active Expired
- 1981-07-31 ES ES504473A patent/ES8306092A1/es not_active Expired
- 1981-07-31 DD DD81232269A patent/DD201673A5/de unknown
- 1981-07-31 HU HU812244A patent/HU187348B/hu unknown
- 1981-07-31 DK DK342981A patent/DK342981A/da not_active Application Discontinuation
- 1981-07-31 BR BR8104979A patent/BR8104979A/pt unknown
- 1981-08-01 SU SU813316601A patent/SU1176830A3/ru active
- 1981-08-01 KR KR1019810002798A patent/KR850000148B1/ko active
Also Published As
Publication number | Publication date |
---|---|
SU1176830A3 (ru) | 1985-08-30 |
BR8104979A (pt) | 1982-04-20 |
ES504473A0 (es) | 1982-12-01 |
HU187348B (en) | 1985-12-28 |
IL63297A0 (en) | 1981-10-30 |
IL63297A (en) | 1984-05-31 |
EP0045709B1 (fr) | 1984-10-03 |
DK342981A (da) | 1982-02-02 |
EP0045709A1 (fr) | 1982-02-10 |
DD201673A5 (de) | 1983-08-03 |
DE3166482D1 (en) | 1984-11-08 |
KR850000148B1 (ko) | 1985-02-28 |
CA1211470A (en) | 1986-09-16 |
ES8306092A1 (es) | 1982-12-01 |
US4418213A (en) | 1983-11-29 |
IE51457B1 (en) | 1986-12-24 |
IE811738L (en) | 1982-02-01 |
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