NO118062B - - Google Patents
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- NO118062B NO118062B NO161792A NO16179266A NO118062B NO 118062 B NO118062 B NO 118062B NO 161792 A NO161792 A NO 161792A NO 16179266 A NO16179266 A NO 16179266A NO 118062 B NO118062 B NO 118062B
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- parts
- acid
- salts
- alkyl
- sulfuric acid
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000011975 tartaric acid Substances 0.000 claims description 5
- 235000002906 tartaric acid Nutrition 0.000 claims description 5
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001630 malic acid Substances 0.000 claims description 4
- 235000011090 malic acid Nutrition 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 3
- GELXFVQAWNTGPQ-UHFFFAOYSA-N [N].C1=CNC=N1 Chemical group [N].C1=CNC=N1 GELXFVQAWNTGPQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000012435 aralkylating agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007859 condensation product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229940099690 malic acid Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 2
- AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- DYTUAOUIQFNOIH-UHFFFAOYSA-N 2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCC(O)(C(O)=O)C(O)(CC)C(O)=O DYTUAOUIQFNOIH-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- NUANSJJRMWHEHS-UHFFFAOYSA-N 2-n-propan-2-ylbenzene-1,2-diamine Chemical compound CC(C)NC1=CC=CC=C1N NUANSJJRMWHEHS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000009994 optical bleaching Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C3/00—Separating dispersed particles from gases or vapour, e.g. air, by electrostatic effect
- B03C3/34—Constructional details or accessories or operation thereof
- B03C3/86—Electrode-carrying means
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S24/00—Buckles, buttons, clasps
- Y10S24/30—Separable-fastener or required component thereof
- Y10S24/43—Separable-fastener or required component thereof including member having distinct formations and mating member selectively interlocking therewith
- Y10S24/49—Separable-fastener or required component thereof including member having distinct formations and mating member selectively interlocking therewith having mounting means allowing repositioning of member for facilitating interlock
Landscapes
- Electrostatic Separation (AREA)
- Thyristors (AREA)
- Insulators (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Framgangsmåte til framstilling av diimidazolderivater. Process for the production of diimidazole derivatives.
Foreliggende oppfinnelse angår diimidazolderivater med den generelle formel The present invention relates to diimidazole derivatives with the general formula
hvori A betyr en eventuelt substituert aromatisk kjerne, hvor i 2 vicinale kullstoffatomer er forbundet med begge imidazol-kvelstoffatomene, R og R1 betyr vannstoff eller like eller forskjellige substituenter og X betyr vannstoff eller en hydroksylgruppe, og deres salter. Resten A i den angitte formel kan være en- eller flerkjernet. Den kan f. eks. bety en eventuelt med halogen-atomer, alkyl- eller alkoksygrupper substituert naftylen- eller fenylrest. Fortrinsvis er den usubstituert fenylenrest. Substituen-tene R og R, betyr fortrinsvis vannstoff. Dessuten kan de være rester av vilkårlig, f. eks. aromatisk eller heterocyklisk natur. Særlig er det alifatiske eller aralifatiske rester og fortrinsvis laveremolekylære alkyl- eller oksyalkylrester slik som metyl-eller oksyetylresten. Saltene av disse forbindelser kan avledes fra vilkårlige anorga-niske eller organiske syrer, f. eks. av svovelsyre, saltsyre, salpetersyre, maursyre- eller eddiksyre. wherein A means an optionally substituted aromatic nucleus, where in 2 vicinal carbon atoms are connected to both imidazole nitrogen atoms, R and R1 mean hydrogen or the same or different substituents and X means hydrogen or a hydroxyl group, and their salts. The residue A in the given formula can be mononuclear or polynuclear. It can e.g. mean a naphthylene or phenyl residue optionally substituted with halogen atoms, alkyl or alkoxy groups. Preferably, it is an unsubstituted phenylene residue. The substituents R and R preferably mean hydrogen. Moreover, they can be remnants of arbitrary, e.g. aromatic or heterocyclic in nature. In particular, there are aliphatic or araliphatic residues and preferably lower molecular weight alkyl or oxyalkyl residues such as the methyl or oxyethyl residue. The salts of these compounds can be derived from arbitrary inorganic or organic acids, e.g. of sulfuric, hydrochloric, nitric, formic or acetic acid.
Man kommer til de nevnte forbindelser når man omsetter egnede aromatiske o-diaminer eller deres salter eventuelt i nærvær av katalysatorer med eplesyre, vinsyre eller funksjonelle derivater av disse syrer og eventuelt lar alkylerings-, oksal-kylerings- eller aralkyleringsmidler innvirke på de erholdte diimidazoler. The aforementioned compounds are obtained by reacting suitable aromatic o-diamines or their salts, possibly in the presence of catalysts with malic acid, tartaric acid or functional derivatives of these acids and optionally allowing alkylating, oxalkylating or aralkylating agents to act on the obtained diimidazoles.
Blant de aromatiske o-diaminer som egner . seg som utgangsstoffer for fram-gangsmåten, skal forstås slike hvori den ene aminogruppe er primær, mens den an-dre aminogruppe er primær eller sekundær. Silke o-diaminer er f. eks.: o-fenylendiamin, 1,2-naftylendiamin, videre isopropyl-o-fenylendiamin, 1-metoksy-3,4-diaminobensol, 1 -amino-2-mono-metyl-amino-bensol eller l-klor-3,4-diaminobensol. Fortrinsvis anvendes o-fenylendiamin. Som derivater av eplesyre eller vinsyre, som kommer i betraktning i stedet for den frie syre for kondensasjonen, skal i første rekke nevnes estere med laveremolekylare alifatiske alkoholer. Omsetningen mellom kom-ponentene foregår hensiktsmessig ved opp-hetning i nærvær av et inert oppløsnings-middel, eventuelt under tilsetning av katalysatorer til middels høye temperatu-rer, fortrinsvis i en inert gass, f. eks. i en kvelstoffstrøm. Som oppløsningsmiddel anvendes særlig middels konsentrerte vandige mineralsyrer. Også organiske oppløsnings-midler, slik som toluol, xylol kan komme i betraktning. For utførelsen av kondensasjonen har det vist seg gunstig med tem-peraturer på mellom 80—140°. Fortrinsvis ledes omsetningen således at acyleringen av imidazolringslutningen foregår i ett ar-beidstrinn. Det er imidlertid også mulig å acylere diaminene bare i en aminogruppe og å isolere acyleringsproduktet og i et an-net trinn å utføre ringslutningen til diimidazoler. Among the aromatic o-diamines that are suitable . themselves as starting materials for the process, are to be understood as those in which one amino group is primary, while the other amino group is primary or secondary. Silk o-diamines are, for example: o-phenylenediamine, 1,2-naphthylenediamine, further isopropyl-o-phenylenediamine, 1-methoxy-3,4-diaminobenzene, 1-amino-2-mono-methyl-amino-benzene or 1-chloro-3,4-diaminobenzene. Preferably, o-phenylenediamine is used. As derivatives of malic acid or tartaric acid, which come into consideration instead of the free acid for the condensation, esters with lower molecular weight aliphatic alcohols should be mentioned in the first place. The reaction between the components conveniently takes place by heating in the presence of an inert solvent, optionally with the addition of catalysts at moderately high temperatures, preferably in an inert gas, e.g. in a stream of nitrogen. Medium-concentrated aqueous mineral acids are particularly used as solvents. Organic solvents, such as toluene, xylol, can also be considered. Temperatures of between 80 and 140° have proved beneficial for carrying out the condensation. Preferably, the reaction is conducted so that the acylation of the imidazole ring closure takes place in one work step. However, it is also possible to acylate the diamines only in an amino group and to isolate the acylation product and in another step to carry out the cyclization to diimidazoles.
En videre utførelsesform for foreliggende framgangsmåte består i at man i stedet for å kondensere de aromatiske o-diaminer og o-nitroaminer fra den aromatiske rekke med eplesyre, vinsyre eller deres funksjonelle derivater i tilknytning reduseres nitrogruppen på kjent måte og deretter bevirker dannelsen av diimidazolene ved ringslutning. A further embodiment of the present method consists in that instead of condensing the aromatic o-diamines and o-nitroamines from the aromatic series with malic acid, tartaric acid or their functional derivatives in connection, the nitro group is reduced in a known manner and then causes the formation of the diimidazoles by ring closure.
Alkyleringen eller aralkyleringen av diimidazolene, som eventuelt skal foretas, går på vanlig måte, f. eks. ved behandling med alkyl-, oksyalkyl- eller aralkylhaloge-nider, slik som bensylklorid, hensiktsmessig under tilsetning av syrebindende midler. For alkyleringen kan det også anvendes dialkylsulfater, slik som dimetylsulfat. The alkylation or aralkylation of the diimidazoles, which may be carried out, proceeds in the usual way, e.g. by treatment with alkyl, oxyalkyl or aralkyl halides, such as benzyl chloride, suitably with the addition of acid-binding agents. Dialkyl sulphates, such as dimethyl sulphate, can also be used for the alkylation.
De nevnte forbindelser og deres salter er fargeløse eller svakt fargede godt krys-talliserte stoffer, som er temmelig tungt oppløselige i de fleste oppløsningsmidler. De kan anvendes som mellomprodukter til framstilling av tekstilhjelpemidler, særlig til optiske blekningsmidler eller fargestof-fer. Selve forbindelsene virker oksydasjons-hemmende og kan derfor anvendes som be-skyttelsesmiddel for celluloseestere, særlig acetatsilke, mot oksydative beskadigelser. The aforementioned compounds and their salts are colorless or slightly colored well-crystallised substances, which are rather poorly soluble in most solvents. They can be used as intermediate products for the production of textile auxiliaries, particularly for optical bleaching agents or dyes. The compounds themselves have an oxidation-inhibiting effect and can therefore be used as a protective agent for cellulose esters, especially acetate silk, against oxidative damage.
I de følgende eksempler betyr deler vektsdeler, forholdet mellom vektsdel og volumdel er det samme som mellom kilo-gram og liter. Temperaturene er angitt i Celsius-grader. In the following examples, parts mean parts by weight, the ratio between part by weight and part by volume is the same as between kilograms and liters. Temperatures are given in degrees Celsius.
Eksempel 1: Example 1:
2000 deler 40 prosents svovelsyre tilsettes ved utelukkelse av luft under om-røring 432 deler o-fenylendiamin og deretter 268 deler d,l-eplesyre. Deretter øker man temperaturen innen 2 timer inntil svak kokning og omrører den klare oppløs-ning 18—48 timer under utelukkelse av luft ved 105—110°. Deretter avkjøles reaksjonsblandingen til 10—15° og omrøres kaldt noen timer. Den utskilte krystallinske masse filtreres fra, filtermassen vaskes med kaldt vann til kongonøytral og tørkes. Det dannede kondensasjonsprodukt med formelen 2000 parts of 40 percent sulfuric acid are added by excluding air while stirring, 432 parts of o-phenylenediamine and then 268 parts of d,l-malic acid. The temperature is then increased within 2 hours to a gentle boil and the clear solution is stirred for 18-48 hours under the exclusion of air at 105-110°. The reaction mixture is then cooled to 10-15° and stirred cold for a few hours. The separated crystalline mass is filtered off, the filter mass is washed with cold water until Congo neutral and dried. It formed condensation product with the formula
er et svakt gulaktig til grønlig farget pulver som er tungt oppløselig i vann og de vanlige organiske oppløsningsmidler. Det oppløses i konsentrert svovelsyre med lys blå farge. is a slightly yellowish to greenish colored powder that is poorly soluble in water and the usual organic solvents. It dissolves in concentrated sulfuric acid with a light blue color.
Den frie base kan fåes når man til-setter den fortynnede svovelsyreoppløsning av kondensasjonsproduktet alkalier, f. eks. ammoniakk eller vandig natriumhydrok-sydoppløsning og frafiltrerer det utfelte kondensasjonsprodukt, vasker det nøytralt med vann og tørker. Det danner et nesten fargeløst pulver og er klart oppløselig i al-koholisk natriumhydroksydoppløsning. The free base can be obtained when alkalis, e.g. ammonia or aqueous sodium hydroxide solution and filter off the precipitated condensation product, wash it neutrally with water and dry. It forms an almost colorless powder and is readily soluble in alcoholic sodium hydroxide solution.
Mengden av 40 prosents svovelsyre kan også økes eller minskes; videre kan det også benyttes mer konsentrert eller mer fortynnet svovelsyre. The amount of 40 percent sulfuric acid can also be increased or decreased; furthermore, more concentrated or more diluted sulfuric acid can also be used.
Anvender man i stedet for de 2000 deler 40 prosents svovelsyre i ovenstående eksempel 2400 deler 20 pst.'s saltsyre, kommer man til hydrokloridet av kondensasjonsproduktet. If instead of the 2,000 parts of 40 per cent sulfuric acid in the above example, 2,400 parts of 20 per cent hydrochloric acid are used, the hydrochloride of the condensation product is obtained.
For framstilling av derivater av kondensasjonsproduktet kan man gå fram som følger; For the production of derivatives of the condensation product, one can proceed as follows;
a) I en oppløsning av 20 deler natri-umhydroksyd i 600 deler etylalkohol opp-løses ved 35—40° under omrøring 55,6 deler a, p-di- [benzimidazyl- (2) ] -mono-oksyetan. I denne oppløsning dryppes det inn innen 3 timer 63 deler dimetylsulfat, deretter om-rører man ennå 5 timer ved 35—40°. Deretter filtrerer man det dannede a, |3-di-[N-metyl-benzimidazyl- (2) ] -monooksyetan, vasker det med alkohol og vann og tørker det. Det kan omkrystalliseres av alkohol og smelter deretter ved 205—206° og er fargeløse krystaller som lyser sterkt blålig opp i ultraviolett lys. b) Går man fram som beskrevet under a), men erstatter de 63 deler dimetylsulfat med 65 deler bensylklorid, får man a, p-di-[N-bensyl-benzimidazyl-(2)]-monooksyetan, som smelter ved 192—193° og har liknende egenskaper. c) En oppløsning av 60 deler natrium-hydroksyd i 600 deler etylalkohol tilsettes a) In a solution of 20 parts of sodium hydroxide in 600 parts of ethyl alcohol, dissolve at 35-40° with stirring 55.6 parts of a,p-di-[benzimidazyl-(2)]-monooxyethane. 63 parts of dimethylsulphate are dripped into this solution within 3 hours, then the mixture is stirred for a further 5 hours at 35-40°. The a,|3-di-[N-methyl-benzimidazyl-(2)]-monooxyethane formed is then filtered, washed with alcohol and water and dried. It can be recrystallized from alcohol and then melts at 205—206° and are colorless crystals that glow strongly bluish in ultraviolet light. b) If you proceed as described under a), but replace the 63 parts of dimethyl sulfate with 65 parts of benzyl chloride, you get a,p-di-[N-benzyl-benzimidazyl-(2)]-monooxyethane, which melts at 192-193 ° and have similar properties. c) A solution of 60 parts sodium hydroxide in 600 parts ethyl alcohol is added
ved 35—40° 113 deler a,(3-di-[benzidazyl-(2)]-mono-oksyetan-monosulfat under god at 35—40° 113 parts a,(3-di-[benzidazyl-(2)]-mono-oxyethane-monosulphate under good
omrøring. Deretter tilsettes innen 2 timer stirring. Then added within 2 hours
37 deler etylenklorhydrin og deretter om-røres blandingen i 3 timer ved 35—40°. Blandingen helles deretter i kaldt vann, det utfelte produkt frafiltreres, vaskes med vann, tørkes og omkrystalliseres av vandig alkohol. Det erholdte a[benzimidazyl-(2)] 37 parts of ethylene chlorohydrin and then the mixture is stirred for 3 hours at 35-40°. The mixture is then poured into cold water, the precipitated product is filtered off, washed with water, dried and recrystallized from aqueous alcohol. The obtained a[benzimidazyl-(2)]
-6- [N-hydroksy-etyl-benzimidacyl- (2) ] - -6- [N-hydroxy-ethyl-benzimidacyl-(2)] -
mono-oksyetan er et lyst pulver, som lyser opp blålig i ultraviolett lys. mono-oxyethane is a bright powder, which glows bluish in ultraviolet light.
Eksempel 2: Man går fram som i 1. og 2. avsnitt i eksempel 1, men anvender i stedet for de 432 deler o-fenylendiamin ekvivalente mengder 5-klor-l,2-diaminobensol eller 5-metyl-1,2 diaminobensol eller 5-metoksy-1,2-diaminobensol. Man får på denne måte a, p-di-[6-klorbenzimidazyl-(2)]-mono-oksyetan eller a, P-di-[6-metylbenzimida-zyl-(2)]-mono-oksyetan, eller a, p-di-[6-metoksybenzimidazyl-(2)] -mono-oksyetan, henholdsvis monosulfatene av disse kon-densasj onsprodukter. For overføring til derivatene kan man gå fram som beskrevet i eksempel 1 under a), b) eller c). Example 2: Proceed as in paragraphs 1 and 2 in example 1, but instead of the 432 parts o-phenylenediamine equivalent amounts of 5-chloro-1,2-diaminobenzene or 5-methyl-1,2-diaminobenzene are used or 5-Methoxy-1,2-diaminobenzene. In this way a, p-di-[6-chlorobenzimidazyl-(2)]-mono-oxyethane is obtained or a, P-di-[6-methylbenzimidazyl-(2)]-mono-oxyethane, or a, p-di-[6-methoxybenzimidazyl-(2)]-mono-oxyethane, respectively the monosulphates of these condensation products. For transfer to the derivatives, one can proceed as described in example 1 under a), b) or c).
Eksempel 3: 24,4 deler l-monometylamino-2-amino- Example 3: 24.4 parts of 1-monomethylamino-2-amino-
bensol og 13,4 deler eplesyre opphetes med 200 deler 50 prosents svovelsyre i 36 timer ved tilbakeløpskjøler. Etter avkjøling frafiltreres det erholdte kondensasjonsprodukt, vaskes med vann og tørkes. Det erholdte produkt er monosulfatet av a,p-di-[N-metylbenzimidazyl- (2) ] -mono-oksyetan og er et grønlig gult pulver, som er oppløselig i fortynnet svovelsyre. benzol and 13.4 parts of malic acid are heated with 200 parts of 50 per cent sulfuric acid for 36 hours in a reflux condenser. After cooling, the condensation product obtained is filtered off, washed with water and dried. The product obtained is the monosulphate of a,p-di-[N-methylbenzimidazyl-(2)]-mono-oxyethane and is a greenish yellow powder, which is soluble in dilute sulfuric acid.
Den frie base kan fåes ved å tilsette den svovelsure oppløsning ammoniakk. Den er identisk med det produkt som er beskrevet i eksempel 1 under a). The free base can be obtained by adding ammonia to the sulfuric acid solution. It is identical to the product described in example 1 under a).
Eksempel 4: 1000 deler 40 prosents svovelsyre tilsettes under utelukkelse av luft under om-røring 216 deler o-fenylen-diamin og deretter 168 deler vinsyre. Deretter øker man temperaturen i 2 timer til svak kokning og omrører den klare oppløsning i 20—40 timer under utelukkelse av luft ved 105— 110°. Deretter avkjøles reaksjonsblandingen til 10—15° og omrøres noen timer kaldt. Den utskilte krystallinske masse frafiltreres, massen vaskes kongonøytralt med kaldt vann og tørkes. Det dannede kondensasjonsprodukt med formelen Example 4: 1,000 parts of 40 per cent sulfuric acid are added with exclusion of air while stirring, 216 parts of o-phenylenediamine and then 168 parts of tartaric acid. The temperature is then increased for 2 hours to a gentle boil and the clear solution is stirred for 20-40 hours while excluding air at 105-110°. The reaction mixture is then cooled to 10-15° and stirred cold for a few hours. The separated crystalline mass is filtered off, the mass is washed neutrally with cold water and dried. It formed a condensation product with the formula
danner et svakt grønlig hvitt krystallinsk pulver, som er oppløselig i varm fortynnet svovelsyre. forms a faint greenish-white crystalline powder, which is soluble in hot dilute sulfuric acid.
Den frie base kan fåes når man til-setter den fortynnede svovelsyre oppløs-ning av kondensasjonsproduktet vandig ammoniumhydroksydoppløsning og frafiltrerer det utfelte kondensasjonsprodukt, vasker det nøytralt med vann og tørker det. Det er et hvitt pulver. The free base can be obtained by adding aqueous ammonium hydroxide solution to the diluted sulfuric acid solution of the condensation product and filtering off the precipitated condensation product, washing it neutrally with water and drying it. It is a white powder.
Eksempel 5: Man går fram som beskrevet i eksempel 4, men anvender i stedet for o-fenylendiamin en ekvivalent mengde 5-metyl-l,2-diaminobensol eller 5-metoksy--,2-diamino -bensol og får således a,p-di[6-metylbenzi-midazyl-(2)]-dioksyetan eller a, p-di-[6-metoksybenzimidazyl- (2) ] -dioksy-etan. Example 5: Proceed as described in example 4, but use instead of o-phenylenediamine an equivalent amount of 5-methyl-1,2-diaminobenzene or 5-methoxy-,2-diaminobenzene and thus get a,p -di[6-methylbenzimidazyl-(2)]-dioxyethane or α,β-di-[6-methoxybenzimidazyl-(2)]-dioxyethane.
Eksempel 6: 108 deler o-fenylendiamin, 163 deler vinsyredietylester og 500 deler klorbensol opphetes i 24 timer med tilbakeløpskjøler, hvorved den dannede alkohol og det dannede vann avdestilleres fortløpende. Etter avkjøling frafiltreres kondensasjonsproduktet, vaskes med klorbensol og alkohol og tørkes. Det er identisk med det ifølge eksempel 4 erholdte produkt. Example 6: 108 parts o-phenylenediamine, 163 parts diethyl tartaric acid and 500 parts of chlorobenzene is heated for 24 hours with a reflux condenser, whereby the formed alcohol and the formed water are successively distilled off. After cooling, the condensation product is filtered off, washed with chlorobenzene and alcohol and dried. It is identical to the product obtained according to example 4.
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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SE02850/65A SE348651B (en) | 1965-03-05 | 1965-03-05 |
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NO118062B true NO118062B (en) | 1969-11-03 |
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NO161792A NO118062B (en) | 1965-03-05 | 1966-02-22 |
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US (1) | US3501898A (en) |
AT (1) | AT269301B (en) |
BE (1) | BE677389A (en) |
CH (1) | CH434209A (en) |
DE (1) | DE1557001B2 (en) |
DK (1) | DK132424C (en) |
ES (1) | ES323708A1 (en) |
FI (1) | FI44376B (en) |
GB (1) | GB1065184A (en) |
NL (1) | NL149391B (en) |
NO (1) | NO118062B (en) |
SE (1) | SE348651B (en) |
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DE2034628A1 (en) * | 1970-07-13 | 1972-02-03 | Metallgesellschaft Ag | Spray electrodes and distancing systems |
BE795910A (en) * | 1972-03-27 | 1973-06-18 | American Air Filter Co | ELECTRODE HOLDER OF ELECTROSTATIC SEPARATOR |
US3918938A (en) * | 1972-03-27 | 1975-11-11 | American Air Filter Co | Electrode support apparatus for electrical precipitators |
US4099219A (en) * | 1976-12-17 | 1978-07-04 | Xerox Corporation | Coronode tensioning and support arrangement |
FR2427841A1 (en) * | 1978-06-09 | 1980-01-04 | Penarroya Miniere Metall | Radial reactor allowing prolonged contact time - comprises enclosure with plates on rotary shaft and conical deflectors for continuous reaction between prods. in different phases |
US5059218A (en) * | 1989-11-28 | 1991-10-22 | William Pick | Construction for supporting a flexible sheet |
US5296019A (en) * | 1990-06-19 | 1994-03-22 | Neg-Ions (North America) Inc. | Dust precipitation from air by negative ionization |
US7276106B1 (en) * | 2006-04-18 | 2007-10-02 | Oreck Holdings Llc | Electrode wire retaining member for an electrostatic precipitator |
US7481870B2 (en) * | 2006-04-18 | 2009-01-27 | Oreck Holdings, Llc | Electrode wire for an electrostatic precipitator |
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US1572347A (en) * | 1925-07-17 | 1926-02-09 | Beck Joseph | Hook |
DE503495C (en) * | 1927-07-31 | 1930-07-23 | Siemens Schuckertwerke Akt Ges | Attachment of a spray wire for electrical gas cleaning systems |
DE517262C (en) * | 1929-10-05 | 1931-02-02 | Metallgesellschaft Ag | Arrangement of the electrodes, especially the discharge electrodes in electric gas cleaners |
FR980435A (en) * | 1948-12-14 | 1951-05-11 | Purification Ind Des Gaz Soc D | Improvements to electric dust collection devices |
US2708980A (en) * | 1952-11-18 | 1955-05-24 | Western Precipitation Corp | Discharge electrode construction |
US2708488A (en) * | 1953-02-16 | 1955-05-17 | Svenska Flaektfabriken Ab | Arrangement in emitting electrodes |
DE1009163B (en) * | 1954-07-07 | 1957-05-29 | Svenska Flaektfabriken Ab | Procedure for cleaning the electrodes in electrical filters |
US2870861A (en) * | 1955-07-27 | 1959-01-27 | Apra Precipitator Corp | Collector-ionizer electrode |
US2867286A (en) * | 1956-04-23 | 1959-01-06 | Cottrell Res Inc | Discharge electrode tensioning means |
US3027970A (en) * | 1959-01-26 | 1962-04-03 | Honeywell Regulator Co | Fluid cleaning apparatus |
GB1016905A (en) * | 1962-04-10 | 1966-01-12 | Holmes & Co Ltd W C | Improvements in or relating to electrostatic precipitators |
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1965
- 1965-03-05 SE SE02850/65A patent/SE348651B/xx unknown
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1966
- 1966-02-22 NO NO161792A patent/NO118062B/no unknown
- 1966-02-22 GB GB7737/66A patent/GB1065184A/en not_active Expired
- 1966-02-28 AT AT187466A patent/AT269301B/en active
- 1966-03-01 ES ES0323708A patent/ES323708A1/en not_active Expired
- 1966-03-03 DE DE1557001A patent/DE1557001B2/en not_active Withdrawn
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- 1966-03-04 NL NL666602856A patent/NL149391B/en not_active IP Right Cessation
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ES323708A1 (en) | 1967-01-16 |
DK132424B (en) | 1975-12-08 |
CH434209A (en) | 1967-04-30 |
US3501898A (en) | 1970-03-24 |
SE348651B (en) | 1972-09-11 |
DK132424C (en) | 1976-05-10 |
AT269301B (en) | 1969-03-10 |
DE1557001A1 (en) | 1970-03-12 |
NL6602856A (en) | 1966-09-06 |
DE1557001B2 (en) | 1980-03-20 |
BE677389A (en) | 1966-08-01 |
FI44376B (en) | 1971-08-02 |
NL149391B (en) | 1976-05-17 |
GB1065184A (en) | 1967-04-12 |
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