SU582759A3 - Способ получени производных бензазолов - Google Patents

Способ получени производных бензазолов

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Publication number
SU582759A3
SU582759A3 SU7602314150A SU2314150A SU582759A3 SU 582759 A3 SU582759 A3 SU 582759A3 SU 7602314150 A SU7602314150 A SU 7602314150A SU 2314150 A SU2314150 A SU 2314150A SU 582759 A3 SU582759 A3 SU 582759A3
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SU
USSR - Soviet Union
Prior art keywords
carbon atoms
alkylene
alkyl
general formula
indicated
Prior art date
Application number
SU7602314150A
Other languages
English (en)
Inventor
Френцис Попплвелл Элен
Ронелд Кларк Дэвид
Original Assignee
Циба-Гейги Аг, (Фирма)
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Publication date
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Application granted granted Critical
Publication of SU582759A3 publication Critical patent/SU582759A3/ru

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
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    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
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    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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Description

(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ БЕНЗАЗОЛОВ
1
Изобретение относитс  к способу получени  новых производных бензимидазола или бензтриазола, которые могут найти применение в качестве пассиваторов металлов.
Известна реакци  аминометилировани  метилбензиламином бензимидазола (реакци -Манниха) 1 .
С целью получени  новых производных бензимидазола или бензтриазола, обладающих ценными металлопассивирующими свойствами, предлагаетс  способ получени  производных бензазолов общей формулы
N
 -Х уВ
CRiS (I)
Вг
где X - азот или метилова  группа;, R - алкилен - OR, где алкилен с 2 или 3 атомами углерода , водород или алкил с 1-4 атомами углерода или Н - алкилен с 3-18 атомами углерода;
R R, или группа формулы
СНгНц - водород или Rj и RJ - алкил с 1-20 атомами углерода и Яц - арапкил ,с 7-9атомами углерода, который заключаетс  в том, что 1 или 2 мол  соединени  общей формулы
1 («
где Rц имеет указанные значени , подвергают взаимодействию соответственно с 1 или 2 мол ми формальдегида и амином общей формулы или где R и Н имеют указанные значени , при условии, если Кц - указанный аралкил, то Rj и R,j - алкил с 1-20 атомами углерода, при 50-120 С,
В предложенном способе используют формалин или параформальдегид. Количественные соотношени  соединени  общей формулы (И) и формальдегида завис т от того,  вл етс  ли амин первичным или вторичным амином. Соотношение соединени  общей формулы 01Vформальдегид:с1мин составл ет 2:2:1 или 1:1:1, если амин вторичный, то предпочтительно соотношение 1:1:1.
Температура процесса предпочтительно повышенна , . Лучше когда соединение общей (П) реаПЦрует вначале с формальдегидом с получением соответствующего N -метилольного соединени , а.после этого. с afOtHOM.
По предлагаемому способу получают Следующие соединени : 1-диэтанолами1Ю{4етилбенэтриазол; 1-диэтаноламинометилбензимидазал , 1-диизопропанолвмннометилбензтриазол; 1-диизопропанолгы«1нометилбензимидазол; N,N -бис- (l-вбнзтриазолилметил) -зтаноламин ; Kf Ы -бис- {l-бензимидазолилметил) -н -пропаноламин N,N -Сис-(l-бенз триазолилметил)-изопропаноламин;
1-( N -метилэтаноламинометил)- бензтриазоп; N,N -бис-(l-бензимидазолилметил )-3-амино-З-метилбутанол, N|N -бис-(1-бензимидазолилметил) -3-метоксипропиламин; 1-диаллиламиномвтил-2-бутилбензимидазол; -(N -ме тилэтаноламинометил)-2-метилбензимидаэол; Я, И -бис-(l-бензтриазолилмет л )-зтоксизтоксипропиламин; Ы,Ы -вис-О-бензимидазолилметил) -олеиламин; N,N -бис- (l-бенэтриазолилметил )-пальмитолиламин; N,N -бис- (l-беизтриазолилметил) -аллиламин ; N,M -бис-(5- ,оС -диметилбензил-1-бензотриазолилметил )-додециламин; 1-(ди- и -бутиламинометил)-5-( -диметилбензил )-бензтриазол.
Пример. 23,82 ч. бензтриазола и 21,03 ч. диэтаноламина смешивают
с 75 ч. этанола и 6,0 ч.36%-ного водного раствора формальдегида, смесь нагревают до кипени  и кип т т 8 ч. После охлаждени  удал ют растворитель в вакууме водоструйного насоса, полученный продукт сушат азеотропной отгонкой также в вакууме водоструйного насоса, добавл   этанол (3x50 ч.)и получают 1-диэтаноламинометилбензтриазол , выход 80%.
В табл. 1-3 приведены соединени , полученные аналогичным способом.
Дл  аминов с более высоким молекул рным весом врем  кип чени  увеличивают до 16 ч. Твердые продукты перекристаллизовывают из этилацетата.
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Claims (1)

  1. Формула изобретени 
    Способ получени  производных азолов общей фop
    лы
    /BI
    сир
    «2
    отличающийс  тем, чтсУ 1 или 2 мол  соединени  общей формулы
    где X - азот или втилова  группа; RJ - алкилен -ORJ,гдe алкилеи с 2 или 3 атомами углерода, R. - водород или алкил с 1-4 атомами углерода иди R - алкилен с 3-18 атомами углерода
    Rj RI или группа формулы
    R, - fe|- алкил с 1-20 атомами углерода и R«- аралкил с 7-9 aTOMaMtt углерода.
    где R имеет указанные значени ,
    подвергают взаимодействию соответственно с 1 или 2 мол ми формальдегида и амином общей формулы R, {l|NH или RjKH , где R и R имеют указаийые значени  при условии, если Кц - указанный аралкил, то R и Kj - алкил с 1-20 атомами углерода, при 50IZOC .
    Источники информации,прин тые во внимание при экспертизе:
    1 .Hider K.,Hankoviky .Н.О. MannccK reac-Uon of benzimldaiotes and some 2-iubeti tuted.,,«ta Chim., Budapest, 1967, 53(3), 271.
SU7602314150A 1975-01-23 1976-01-20 Способ получени производных бензазолов SU582759A3 (ru)

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DE3376651D1 (en) * 1982-02-26 1988-06-23 Ciba Geigy Ag Mixtures of benzotriazoles, process for their preparation and their use as metal passivators
GB2152073B (en) * 1983-12-23 1986-10-22 Ciba Geigy Lubricant stabilizer additives
JPS63191514U (ru) * 1987-05-28 1988-12-09
JPH01127127U (ru) * 1988-02-25 1989-08-30
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US4997585A (en) * 1990-03-30 1991-03-05 Exxon Research And Engineering Company Aromatic substituted benzotriazole containing lubricants having improved oxidation stability
GB9013142D0 (en) * 1990-06-13 1990-08-01 Ciba Geigy Ag Chemical compounds useful as metal deactivators
JPH06100881A (ja) * 1992-09-18 1994-04-12 Kyoseki Seihin Gijutsu Kenkyusho:Kk 冷凍機油組成物
US5441563A (en) * 1993-07-06 1995-08-15 Armstrong World Industries, Inc. Highly insoluble azole embossing inhibitor and the use thereof
TW399094B (en) * 1995-04-11 2000-07-21 Ciba Sc Holding Ag Compounds with (benzo)triazole radicals
US5548003A (en) * 1995-08-14 1996-08-20 Armstrong World Industries, Inc. Azole-aldehyde addition product embossing inhibitors and the use thereof
US5622922A (en) * 1995-12-27 1997-04-22 Exxon Chemical Patents Inc. Method of solubilizing a benzotriazole with a thiadiazole
US5824721A (en) * 1996-06-10 1998-10-20 Armstrong World Industries, Inc. Water soluble triazole derivative embossing inhibitor and the use thereof
JP3702069B2 (ja) * 1997-05-07 2005-10-05 東洋アルミニウム株式会社 アルミニウム顔料組成物
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