[go: up one dir, main page]

NO127607B - - Google Patents

Download PDF

Info

Publication number
NO127607B
NO127607B NO04270/69A NO427069A NO127607B NO 127607 B NO127607 B NO 127607B NO 04270/69 A NO04270/69 A NO 04270/69A NO 427069 A NO427069 A NO 427069A NO 127607 B NO127607 B NO 127607B
Authority
NO
Norway
Prior art keywords
acid
general formula
hydrazine
hydrazide
nicotinic acid
Prior art date
Application number
NO04270/69A
Other languages
Norwegian (no)
Inventor
G Rath
E Ferfers
E Hasselhoff
Original Assignee
Solvay Werke Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Solvay Werke Gmbh filed Critical Solvay Werke Gmbh
Publication of NO127607B publication Critical patent/NO127607B/no

Links

Classifications

    • G—PHYSICS
    • G05—CONTROLLING; REGULATING
    • G05D—SYSTEMS FOR CONTROLLING OR REGULATING NON-ELECTRIC VARIABLES
    • G05D11/00—Control of flow ratio
    • G05D11/02—Controlling ratio of two or more flows of fluid or fluent material
    • G05D11/13—Controlling ratio of two or more flows of fluid or fluent material characterised by the use of electric means
    • G05D11/131—Controlling ratio of two or more flows of fluid or fluent material characterised by the use of electric means by measuring the values related to the quantity of the individual components
    • G05D11/132—Controlling ratio of two or more flows of fluid or fluent material characterised by the use of electric means by measuring the values related to the quantity of the individual components by controlling the flow of the individual components
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
    • B01F25/50—Circulation mixers, e.g. wherein at least part of the mixture is discharged from and reintroduced into a receptacle
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F33/00—Other mixers; Mixing plants; Combinations of mixers
    • B01F33/80—Mixing plants; Combinations of mixers
    • B01F33/84—Mixing plants with mixing receptacles receiving material dispensed from several component receptacles, e.g. paint tins
    • B01F33/841—Mixing plants with mixing receptacles receiving material dispensed from several component receptacles, e.g. paint tins with component receptacles fixed in a circular configuration on a horizontal table, e.g. the table being able to be indexed about a vertical axis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F35/00—Accessories for mixers; Auxiliary operations or auxiliary devices; Parts or details of general application
    • B01F35/80—Forming a predetermined ratio of the substances to be mixed
    • B01F35/83—Forming a predetermined ratio of the substances to be mixed by controlling the ratio of two or more flows, e.g. using flow sensing or flow controlling devices
    • B01F35/834—Forming a predetermined ratio of the substances to be mixed by controlling the ratio of two or more flows, e.g. using flow sensing or flow controlling devices the flow of substances to be mixed circulating in a closed circuit, e.g. from a container through valve, driving means, metering means or dispensing means, e.g. 3-way valve, and back to the container
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F2101/00—Mixing characterised by the nature of the mixed materials or by the application field
    • B01F2101/30—Mixing paints or paint ingredients, e.g. pigments, dyes, colours, lacquers or enamel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Automation & Control Theory (AREA)
  • Coating Apparatus (AREA)
  • Nozzles (AREA)
  • Pyridine Compounds (AREA)
  • Mixers Of The Rotary Stirring Type (AREA)
  • Accessories For Mixers (AREA)

Description

Fremgangsmåte for fremstilling av nikotinsyrehydrazid-derivater. Process for the production of nicotinic acid hydrazide derivatives.

Foreliggende oppfinnelse angår fremstillingen av nye nikotinsyrehydrazinderi-vater og salter av disse forbindelser, og er The present invention relates to the production of new nicotinic acid hydrazine derivatives and salts of these compounds, and is

karakterisert ved at man fremstiller en characterized by producing a

forbindelse med den generelle formel: connection with the general formula:

i hvilken Ri betyr hydrogen eller metyl og Ro en ikke-aromatisk kullvannstoffrest med 2—7 kullstoffatomer, såvel som deres salter, enten ved kondensasjon av en syre av den generelle formel: med et substituert hydrazin med den generelle formel: in which Ri is hydrogen or methyl and Ro is a non-aromatic hydrocarbon residue of 2-7 carbon atoms, as well as their salts, either by condensation of an acid of the general formula: with a substituted hydrazine of the general formula:

i hvilken Ri og R2 har forannevnte betyd-ning, i nærvær av et karbodiimid og eventuelt overføring i et salt, eller etter i og in which R1 and R2 have the aforementioned meaning, in the presence of a carbodiimide and possibly transfer in a salt, or after i and

for seg kjente metoder. known methods.

På den ene side vedrører nærværende On the one hand, the present concerns

oppfinnelse en ny fremgangsmåte for fremstilling av nikotinsyrehydrazidderivater. invention a new method for the production of nicotinic acid hydrazide derivatives.

Etter denne fremgangsmåte kondenseres After this procedure is condensed

en eventuelt i ringen metylsubstituert nikotinsyre med et substituert hydrazin i an optionally methyl-substituted nicotinic acid in the ring with a substituted hydrazine i

nærvær av et karbodiimid. For omsetnin-gen kan syrene eller deres salter direkte presence of a carbodiimide. For the turnover, the acids or their salts can directly

anvendes. En omdannelse i de reaksjons- are used. A transformation in the reaction

dyktigere estere, halogenider etc. er ikke nødvendig. De som kondensasjonsmiddel anvendte N,N'-disubstituerte karbodiimider kan f. eks. fremstilles ved behandling av disubstituerte urinstoffderivater med p-toluol-sulfoklorid i pyridin. Ved reaksjonen etter oppfinnelsen gjenvinnes de tilsvarende urinstoffderivater. Ved anvendel-se av egnede substituerte karbodiimider, f. eks. N,N'-dicykloheksylkarbodiimid, får man som biprodukter urinstoffderivater som lett kan skilles fra reaksjonsproduk-tet. Reaksjonen kan gjennomføres ved en temperatur mellom 0 og 50°, fortrinnsvis ved en romtemperatur eller svakt forhøyet temperatur. Det er hensiktsmessig å an-vende et oppløsningsmiddel. Det kan velges såvel et organisk oppløsningsmiddel, f. eks. metylenklorid, kloroform, dioksan, tetra-hydrofuran, dimetylformamid eller aceto-nitril, som vann. more capable esters, halides, etc. are not required. The N,N'-disubstituted carbodiimides used as condensation agents can e.g. is prepared by treating disubstituted urea derivatives with p-toluene sulphochloride in pyridine. In the reaction according to the invention, the corresponding urea derivatives are recovered. When using suitable substituted carbodiimides, e.g. N,N'-dicyclohexylcarbodiimide, urea derivatives are obtained as by-products which can be easily separated from the reaction product. The reaction can be carried out at a temperature between 0 and 50°, preferably at room temperature or slightly elevated temperature. It is appropriate to use a solvent. An organic solvent can be chosen as well, e.g. methylene chloride, chloroform, dioxane, tetrahydrofuran, dimethylformamide or acetonitrile, such as water.

På den annen side vedrører nærværende oppfinnelse fremstillingen av nikotin-syrehydrazider etter i og for seg kjente metoder. Med utrykket «kjente metoder» skal forstås metoder som er åpenbart i den kjemiske litteratur. F. eks. kan eventuelt i pyridinkjernen metylerte reaksjonsdykti-ge nikotinsyrederivater, som f. eks. lavere alkylestre, halogenider, eller amider av denne syre omsettes med et tilsvarende substituert hydrazin. Man kan også omset-te i pyridinkjernen metylert nikotinsyrehydrazid med en karbonylforbindelse og hy-drere det erholdte nikotinoylhydrazon av karbonylforbindelsen samtidig eller etter-, på. Hydreringen utføres hensiktsmessig.-; On the other hand, the present invention relates to the preparation of nicotinic acid hydrazides according to methods known per se. The term "known methods" is understood to mean methods that are obvious in the chemical literature. For example can optionally methylate reactive nicotinic acid derivatives in the pyridine nucleus, such as e.g. lower alkyl esters, halides or amides of this acid are reacted with a correspondingly substituted hydrazine. One can also react in the pyridine nucleus methylated nicotinic acid hydrazide with a carbonyl compound and hydrate the obtained nicotinyl hydrazone of the carbonyl compound at the same time or afterwards. The hydration is carried out appropriately.-;

nærvær av katalysatorer som f. ékS. platirr-' presence of catalysts such as ékS. platirr-'

oksyd, palladiumkull, osv. fortrinsvis i et inert oppløsningsmiddel. Ifølge en variant av sistnevnte reaksjon kan man også om-sette nikotinoylhydrazonet med en Grignard-forbindelse og hydrolysere addisjons-produktet. oxide, palladium charcoal, etc. preferably in an inert solvent. According to a variant of the latter reaction, one can also react the nicotinoyl hydrazone with a Grignard compound and hydrolyze the addition product.

Etter fremgangsmåten ifølge oppfinnelsen kan f. eks. følgende nikotinsyrehydrazidderivater utvinnes: 1-nikotinoyl-2-propyl-hydrazin, 1 -nikotinoyl-2-isobutyl-hydrazin, l-nikotinoyl-2-heptyl-hydrazin, 1 -nikotinoyl-2 -isopropyl-hydrazin, 1 -nikotinoyl-2 - [ butyl- (2') ] -hydrazin, 1 -nikotinoyl-2- [ pentyl- (3') ] -hydrazin, 1 -nikotinoyl-2-[4'-metyl-pentyl-(2') ] -hydrazin, 1-nikotinoyl-2-cyklopropyl-hydrazin, 1-nikotinoy 1 - 2 -cykloheksyl-hy drazin, 1 -nikotinoy 1- 2 - According to the method according to the invention, e.g. the following nicotinic acid hydrazide derivatives are recovered: 1-nicotinoyl-2-propyl-hydrazine, 1-nicotinoyl-2-isobutyl-hydrazine, 1-nicotinoyl-2-heptyl-hydrazine, 1-nicotinoyl-2-isopropyl-hydrazine, 1-nicotinoyl-2- [butyl-(2')]-hydrazine, 1-nicotinoyl-2-[pentyl-(3')]-hydrazine, 1-nicotinoyl-2-[4'-methyl-pentyl-(2')]-hydrazine, 1-nicotinoyl-2-cyclopropyl-hydrazine, 1-nicotinoy 1 - 2 -cyclohexyl-hydrazine, 1 -nicotinoy 1- 2 -

(a-cyklo-pentyl-etyl)-hydrazin, 1-nikotinoyl-2-tert. butyl-hydrazin, l-(6'-metyl-nikotinoyl) -2-isopropyl-hydrazin, 1-nikotinoyl-2-cyklopentyl-hydrazin. (a-cyclo-pentyl-ethyl)-hydrazine, 1-nicotinoyl-2-tert. butyl-hydrazine, 1-(6'-methyl-nicotinoyl)-2-isopropyl-hydrazine, 1-nicotinoyl-2-cyclopentyl-hydrazine.

De nikotinsyrehydrazidderivater som oppnåes ifølge oppfinnelsen danner velde-finerte salter, såvel med anorganiske som med organiske syrer, f. eks. med halogen-vannstoffsyrer, som klorvannstoffsyre, bromvannstoffsyre, jodvannstoffsyre, med andre mineralsyrer som svovelsyre, fosfor-syre, salpetersyre, og med organiske syrer, som vinsyre, sitronsyre, kamfersulfosyre, etansulfosyre, salicylsyre, askorbinsyre, maleinsyre, mandelsyre osv. Foretrukne salter er hydrohalogenider, særlig hydro-klorid. Syreaddisjonssaltene fremstilles fortrinsvis i et inert oppløsningsmiddel ved behandling av hydrazinderivatet med et overskudd av den tilsvarende syre. The nicotinic acid hydrazide derivatives obtained according to the invention form well-defined salts, both with inorganic and organic acids, e.g. with halogen-hydrogen acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, with other mineral acids such as sulfuric acid, phosphoric acid, nitric acid, and with organic acids, such as tartaric acid, citric acid, camphorsulfonic acid, ethanesulfonic acid, salicylic acid, ascorbic acid, maleic acid, mandelic acid, etc. Preferred salts are hydrohalides, especially hydrochloride. The acid addition salts are preferably prepared in an inert solvent by treating the hydrazine derivative with an excess of the corresponding acid.

Produktene etter fremgangsmåten ifølge oppfinnelsen og deres salter hemmer monoaminoksydase. Enkelte representanter utmerker seg ved sin utpregede antidepres-sive virkning og virker ved kachexia vekt-økende. De er således en verdifull tilvekst til legemidlene. The products according to the method according to the invention and their salts inhibit monoamine oxidase. Certain representatives are distinguished by their pronounced anti-depressant effect and have a weight-increasing effect in cachexia. They are thus a valuable addition to the medicines.

Eksempel 1. Example 1.

l-nikotinoyl-2-isopropyl-hydrazin. 1-nicotinoyl-2-isopropyl-hydrazine.

En oppløsning av 12,3 g nikotinsyre og 10,1 g trietylamin røres i 150 cm3 acetoni-tril en halv time med 11,05 g isopropyl-hydrazin, hvorpå 20,63 g dicykloheksylkar-bodiimid tilsettes., Temperaturen stiger til a"begynne med-svakt og holdes ved av-kjøling l under 30°...Etter. 4. timers omrøring fitør-ere&fr^ det utskilte-N,N'-dicykloheksyl-ijrj[ns.tQf,f,,og Jiltratet dampes inn. Resten ekstraheres. ved: 40" rneij 500; cm<3> benzol, betlzolen. dampes av, og resten behandles m£d .100 cm3 vann. Den vandige oppløsning inndampes til tørrhet, og resten bringes til krystallisasjon ved behandling med eter. Etter omkrystallisasjon fra benzol får man fargeløse krystaller med smeltepunkt på 104—105°. A solution of 12.3 g of nicotinic acid and 10.1 g of triethylamine is stirred in 150 cm3 of acetonitrile for half an hour with 11.05 g of isopropyl hydrazine, after which 20.63 g of dicyclohexyl carbodiimide is added. The temperature rises to a"start with-weak and kept on cooling below 30°... After 4 hours of stirring, the separated N,N'-dicyclohexyl-ijrj[ns.tQf,f,,and the nitrate are evaporated. The residue is extracted at: 40" rneij 500; cm<3> benzene, betlzolene. is evaporated, and the residue is treated with £d .100 cm3 of water. The aqueous solution is evaporated to dryness, and the residue is brought to crystallisation by treatment with ether. After recrystallization from benzene, colorless crystals with a melting point of 104-105° are obtained.

Eksempel 2. Example 2.

1 -niko tinoyl - 2 - [ buty 1 - (2') ] -hy drazin. 1 -nico tinoyl - 2 - [ buty 1 - (2') ] -hy drazin.

En oppløsning av 12,3 g nikotinsyre og 8,8 g butyl-(2)-hydrazin i 150 cm<3> acetoni-tril tilsettes 20,63 g dicykloheksyl-karbodiimid og røres i 4 timer. Til å begynne med kjøles reaksjonskaret for at temperaturen skal være under 30°. Man filtrerer fra ut-skilt N,N'-dicykloheksylurinstoff og dam-per filtratet inn. Resten behandles med 200 cm<3> vann ved 40°, den vandige oppløsning dampes inn, og resten destilleres, kokepunkt 116 70,03 mm. Destillatet stivner til en kry-stallmasse. A solution of 12.3 g of nicotinic acid and 8.8 g of butyl-(2)-hydrazine in 150 cm<3> of acetonitrile is added to 20.63 g of dicyclohexylcarbodiimide and stirred for 4 hours. To begin with, the reaction vessel is cooled so that the temperature is below 30°. The separated N,N'-dicyclohexylurea is filtered and the filtrate is evaporated. The residue is treated with 200 cm<3> of water at 40°, the aqueous solution is evaporated, and the residue is distilled, boiling point 116 70.03 mm. The distillate solidifies into a crystalline mass.

Eksempel 3. Example 3.

1 -nikotinoyl -2 -isopropyl-hydrazin 1-nicotinoyl-2-isopropyl-hydrazine

40 g nikotinsyrehydrazid kokes i 650 cm3 aceton til klar oppløsning, hvorpå der inndampes til tørrhet, resten tørkes på lei-re og omkrystalliseres en gang fra benzol/ aceton 5:1. 40 g av det slik erholdte 1-nikotinoyl-2-isopropyliden-hydrazin hydreres i 1000 cm3 metanol under tilsetning av platinoksyd under normale betingelser inntil opptagelse av den beregnete mengde hydrogen (1 mol pr. mol innsatt masse). Det konsentrerte filtrat opptas i 500 cm3 etanol, tilsettes 32 g oksalsyre og klares etter kjø-ling i isskap ved filtrering. Fra filtratet faller etter ny oppbevaring i kulde 17 g rått aoksalat ut, som flere ganger omkrystalliseres fra etanol under tilsetning av dyre-kull. Man får således l-nikotinoyl-2-isopropyl-hydrazin i form av sesqui-oksalat med smeltepunkt på 139—141°. 40 g of nicotinic acid hydrazide is boiled in 650 cm3 of acetone to a clear solution, after which it is evaporated to dryness, the residue is dried on clay and recrystallized once from benzene/acetone 5:1. 40 g of the 1-nicotinoyl-2-isopropylidene hydrazine thus obtained is hydrogenated in 1000 cm 3 of methanol with the addition of platinum oxide under normal conditions until the calculated amount of hydrogen is taken up (1 mol per mol of mass inserted). The concentrated filtrate is taken up in 500 cm3 of ethanol, 32 g of oxalic acid is added and clarified after cooling in an icebox by filtration. After further storage in the cold, 17 g of crude oxalate fall out of the filtrate, which is recrystallized several times from ethanol with the addition of animal charcoal. One thus obtains 1-nicotinoyl-2-isopropyl-hydrazine in the form of sesqui-oxalate with a melting point of 139-141°.

Eksempel 4. l-(6'-metyl-nikotinoyl) -2-isopropyl-hydrazin. Example 4. 1-(6'-methyl-nicotinoyl)-2-isopropyl-hydrazine.

15 g 6-metyl-nikotinsyrehydrazid, er-holdt ved omsetning av 6-metyl-nikotin-syreetylester med hydrazinhydrat i etanolsk 15 g of 6-methyl-nicotinic acid hydrazide, obtained by reacting 6-methyl-nicotinic acid ethyl ester with hydrazine hydrate in ethanolic

oppløsning, kokes 3 timer med 250 cm3 aceton, konsentreres til tørrhet i vakuum, og resten omkrystalliseres fra benzol. De erholdte 15 g l-(6'-metyl-nikotinoyl)-2-iso-propyliden-hydrazin hydreres i 300 cm<3 >etanol under tilsetning av platinoksyd under normalbetingelser inntil opptagelse av den beregnede mengde hydrogen. Det fra solution, boiled for 3 hours with 250 cm3 of acetone, concentrated to dryness in vacuo, and the residue recrystallized from benzene. The 15 g of 1-(6'-methyl-nicotinoyl)-2-iso-propylidene-hydrazine obtained are hydrogenated in 300 cm<3 >ethanol with the addition of platinum oxide under normal conditions until the calculated amount of hydrogen is taken up. That from

katalysatoren avnutschede filtrat bringes the catalyst avnschede filtrate is brought

til tørrhet i vakuum, og resten omkrystalliseres noen ganger fra petroleter/etanol. to dryness in vacuo, and the residue recrystallized a few times from petroleum ether/ethanol.

Man får således l-(6'-metyl-nikotinoyl)-2-isopropyl-hydrazin med smeltepunkt 117-118,5°. One thus obtains 1-(6'-methyl-nicotinoyl)-2-isopropyl-hydrazine with a melting point of 117-118.5°.

Eksempel 5. Example 5.

1 -nikotinoyl-2 -cykloheksyl-hydrazin. 1-nicotinoyl-2-cyclohexyl-hydrazine.

20 g nikotinsyrehydrazid og 11 g cyklo-heksanon hydreres i 300 cm<:t> etanol under 20 g of nicotinic acid hydrazide and 11 g of cyclohexanone are hydrated in 300 cm<:t> of ethanol under

tilsetning av platinoksyd ved normalbetingelser inntil opptagelse av en ekvivalent addition of platinum oxide under normal conditions until absorption of one equivalent

hydrogen. Det fra katalysatoren avnutschede filtrat bringes til tørrhet i vakuum, og hydrogen. The filtrate extracted from the catalyst is brought to dryness in a vacuum, and

resten omkrystalliseres fra petroleter. Det the residue is recrystallized from petroleum ether. The

erholdte l-nikotinoyl-2-cykloheksylhydra-zin smelter ved 119—121°. 1-nicotinoyl-2-cyclohexylhydrazine obtained melts at 119-121°.

Eksempel 6. Example 6.

l-nikotinoyl-2-isopropyl-hydrazin. 1-nicotinoyl-2-isopropyl-hydrazine.

20 g nikotinsyremetylester oppvarmes 20 g of nicotinic acid methyl ester are heated

med 20 g isopropyl-hydrazin under uteluk-kelse av luft i 10 timer ved 100°. Derpå de-stillerer man av overskuddet av isopropyl-hydrazin og det dannede metanol og iso-lerer l-nikotinoyl-2-isopropyl-hydrazinet with 20 g of isopropyl hydrazine under exclusion of air for 10 hours at 100°. The excess of isopropyl-hydrazine and the methanol formed are then distilled and the 1-nicotinoyl-2-isopropyl-hydrazine is isolated

som i eksempel 3 som sesqui-oksalat med as in example 3 as sesqui-oxalate with

smeltepunkt på 139—141°. melting point of 139-141°.

Claims (5)

1. Fremgangsmåte for fremstilling av1. Procedure for the production of nikotinsyrederivater med den generelle formel: i hvilken Ri betyr hydrogen eller metyl, og Ro en ikke-aromatisk kullvannstoffrest med 2—7 kullstoffatomer, såvel som deres salter, karakterisert ved at man kondenserer en syre med den generelle formel: med et substituert hydrazin med den generelle formel: i hvilken Ri og R2 har foran nevnte betyd-ning, i nærvær av et karbodiimid, eller at man omsetter et reaksjonsdyktig derivat av en syre med den generelle formel II med et substituert hydrazin med den generelle formel III, eller at man kondenserer et hydrazid av en syre med den generelle formel II med en karbonylforbindelse med 2—7 kullstoffatomer og hydrerer det dannede hydrazon samtidig eller etterpå, eller at man kondenserer hydrazidet av en syre med den generelle formel II med en ikke-aromatisk karbonylforbindelse med 2—7 kullstoffatomer, behandler det dannede hydrazon med en Grignard-forbindelse og hydrolyserer det oppståtte addisjonspro-dukt, og eventuelt overfører de dannede nikotinsyrehydrazidderivater i et salt. nicotinic acid derivatives with the general formula: in which Ri means hydrogen or methyl, and Ro a non-aromatic hydrocarbon residue with 2-7 carbon atoms, as well as their salts, characterized by condensing an acid with the general formula: with a substituted hydrazine of the general formula: in which R1 and R2 have the previously mentioned meaning, in the presence of a carbodiimide, or that one reacts a reactive derivative of an acid of the general formula II with a substituted hydrazine of the general formula III, or that one condenses a hydrazide of an acid of the general formula II with a carbonyl compound of 2-7 carbon atoms and hydrate the formed hydrazone simultaneously or afterwards, or that one condenses the hydrazide of an acid of the general formula II with a non-aromatic carbonyl compound of 2-7 carbon atoms, treating the formed hydrazone with a Grignard compound and hydrolyzes the resulting addition product, and optionally transfers the formed nicotinic acid hydrazide derivatives in a salt. 2. Fremgangsmåte etter påstand 1, karakterisert ved at man kondenserer en syre med den generelle formel II med et substituert hydrazin med den generelle formel III eventuelt i et oppløsningsmiddel ved en temperatur mellom 15 og 30°, og i nærvær av et karbodiimid, f. eks. dicyklo-heksylkarbodiimid. 2. Process according to claim 1, characterized in that an acid of the general formula II is condensed with a substituted hydrazine of the general formula III, optionally in a solvent at a temperature between 15 and 30°, and in the presence of a carbodiimide, e.g. e.g. dicyclohexylcarbodiimide. 3. Fremgangsmåte etter påstand 1, karakterisert ved at man anvender som reaksjonsdyktig syrederivat en ester, et halo-genid eller anhydridet. 3. Method according to claim 1, characterized in that an ester, a halide or an anhydride is used as a reactive acid derivative. 4. Fremgangsmåte etter påstand 1, karakterisert ved det ved omsetning med nikotinsyrehydrazidet med karbonylforbindelsen dannede hydrazon hydreres kataly-tisk, f. eks. i nærvær av platinaoksyd eller palladiumkull. 4. Method according to claim 1, characterized in that the hydrazone formed by reaction with the nicotinic acid hydrazide with the carbonyl compound is hydrogenated catalytically, e.g. in the presence of platinum oxide or palladium charcoal. 5. Fremgangsmåte etter påstand 1 og 4, karakterisert ved at man som karbonylforbindelse anvender aceton.5. Method according to claims 1 and 4, characterized in that acetone is used as the carbonyl compound.
NO04270/69A 1968-10-29 1969-10-28 NO127607B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1805853A DE1805853C3 (en) 1968-10-29 1968-10-29 Device for setting, dosing and mixing color tones

Publications (1)

Publication Number Publication Date
NO127607B true NO127607B (en) 1973-07-23

Family

ID=5711856

Family Applications (1)

Application Number Title Priority Date Filing Date
NO04270/69A NO127607B (en) 1968-10-29 1969-10-28

Country Status (10)

Country Link
AT (1) AT306190B (en)
BE (1) BE740881A (en)
CH (1) CH508494A (en)
DE (1) DE1805853C3 (en)
ES (1) ES372428A1 (en)
FR (1) FR2021811A1 (en)
GB (1) GB1272258A (en)
NL (1) NL6916237A (en)
NO (1) NO127607B (en)
SE (1) SE362387B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1037638B (en) * 1975-04-24 1979-11-20 Arrigoni G STORAGE AND DISTRIBUTION PLANT FOR KITCHEN PRODUCTS COLORS FOR FABRIC PRINTING
DE2807423C2 (en) * 1978-02-22 1985-11-21 Jochen 4300 Essen Barry Jun. Device for adjusting, metering and mixing colors for the production of paints and the like
DK112386D0 (en) * 1986-03-11 1986-03-11 On Computer Electronics A S DEVICE AND METHOD FOR DOSING LIQUID MEDIA
FI78420C (en) * 1987-03-20 1989-08-10 Cimcorp Oy Målfärgnyanseringsmaskin
FI76290C (en) * 1987-03-20 1988-10-10 Cimcorp Oy Målfärgnyanseringsmaskin
DE9301147U1 (en) * 1993-01-28 1993-07-08 BVS Beratung Verkauf Service Grafische Technik GmbH, 8901 Stadtbergen Device for supplying a paint consumer with different colors
FI103500B1 (en) * 1995-02-03 1999-07-15 Ruutteri Oy Method and apparatus for dispensing and mixing liquid substances
DE10361103A1 (en) * 2003-12-22 2005-07-21 SCHÜTZE, Thomas Multicolour mixing head
EP2143485A3 (en) * 2005-04-07 2010-03-31 Hero Europe S.r.L. Modular dye meter
US8528781B2 (en) 2005-04-07 2013-09-10 Hero Europe S.R.L. Modular dye meter and method of preparing compounds
FR2926186B1 (en) * 2008-01-14 2012-12-07 Atelier Dorez DEVICE AND METHOD FOR PREPARING DOSES OF COATING COIL
US8224481B2 (en) * 2009-01-19 2012-07-17 Access Business Group International Llc Method and apparatus for dispensing fluid compositions
ITTO20120773A1 (en) * 2012-09-06 2012-12-06 Start Up S R L REFINED CARTRIDGE FOR PORTABLE AUTOMATIC DISPENSER AND AUTOMATIC PORTABLE DISPENSER EQUIPPED WITH SUCH CARTRIDGES.
CN102877251B (en) * 2012-09-19 2014-11-19 绍兴卓信染整科技有限公司 Full-automatic size mixing and liquid preparation system for dyeing and printing and liquid preparation method
IT201800006192A1 (en) * 2018-06-11 2019-12-11 MACHINE AND PROCEDURE FOR DISPENSING FLUID PRODUCTS, IN PARTICULAR COLORING LIQUIDS
CN110370859A (en) * 2019-07-19 2019-10-25 平顶山学院 A kind of Multifunctional painting pigment spray equipment
CN111905595A (en) * 2020-07-30 2020-11-10 广州昊方汽车零部件有限公司 A paint agitating unit for automobile parts production
CN113731288B (en) * 2021-09-18 2024-08-20 娄底彤艳新材料科技有限公司 A piece together and mix device for organic pigment is stable to be pieced together
CN115416426B (en) * 2022-10-08 2023-06-02 河南城建学院 Color mixing device capable of adding pigment in trace amount
CN119016003B (en) * 2024-10-28 2025-02-11 山东鹏展医疗科技有限公司 Unitary peroxyacetic acid preparation mixing device and production process

Also Published As

Publication number Publication date
AT306190B (en) 1973-03-26
DE1805853A1 (en) 1970-09-10
CH508494A (en) 1971-06-15
BE740881A (en) 1970-04-28
SE362387B (en) 1973-12-10
NL6916237A (en) 1970-05-04
DE1805853C3 (en) 1974-07-11
FR2021811A1 (en) 1970-07-24
ES372428A1 (en) 1971-10-16
DE1805853B2 (en) 1973-12-13
GB1272258A (en) 1972-04-26

Similar Documents

Publication Publication Date Title
NO127607B (en)
NO127606B (en)
SU584770A3 (en) Method of preparing derivatives of 2,4-diaminopyrimidine 3-oxide
US5424432A (en) Process for the preparation of imidazolutidine
NO309324B1 (en) Process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl) -1H-indole-5-ethanesulfonamides
NO130797B (en)
US3201406A (en) Pyridylcoumarins
SU576938A3 (en) Method of preparing 8-aminomethylisoflavone derivatives or salts thereof
NO128543B (en)
US4827020A (en) Propargyl amide precursor to 1-propargyl-2,4-dioxoimidazolidine
JPS638368A (en) 4-benzyloxy-3-pyrroline-2-one-1-ylacetamide,manufacture and use
US4596884A (en) 4-(2-phenoxyethyl)-1,2,4-triazolone process intermediates
SU682128A3 (en) Method of preparation of 1-alkyl-3-oxy-5-chloro-1,2,4-triazols or salts thereof
EP0062068B1 (en) N-phthalidyl-5-fluorouracil derivatives
AU2004232454B2 (en) Method for the production of nicotinaldehydes
US2724710A (en) 4-pyridazinecarboxylic acid and salts thereof with bases
JP2767295B2 (en) Method for producing indole-3-carbonitrile compound
US5204464A (en) High bulk density, crystalline 3-cyano-2-morpholino-5-pyrid-4-yl)-pyridine
US4376860A (en) Pyridyl ketone
US3255186A (en) 3-(pyridyl)-2h-1, 4-benzoxazin-2-ones
SU668596A3 (en) Method of producing oxime derivatives or salts thereof
US4579954A (en) Cimetidine monohydrate
US4077977A (en) Ethenoanthracenes
NO128546B (en)
SU584781A3 (en) Method of preparing 1-acylhomopyrimidazole derivatives or salts thereof