NO125153B - - Google Patents
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- NO125153B NO125153B NO169958A NO16995867A NO125153B NO 125153 B NO125153 B NO 125153B NO 169958 A NO169958 A NO 169958A NO 16995867 A NO16995867 A NO 16995867A NO 125153 B NO125153 B NO 125153B
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- Norway
- Prior art keywords
- benzene
- disulfonate
- naphthalene
- parts
- disulfonic
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 11
- 239000012298 atmosphere Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910001385 heavy metal Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- SPSBOOGCFYQPSD-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].[Na].C1=CC=CC=C1 SPSBOOGCFYQPSD-UHFFFAOYSA-N 0.000 description 6
- GTRLQRHWPXEBLF-UHFFFAOYSA-N benzyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=CC=C1 GTRLQRHWPXEBLF-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PFVJLGPIYRQLHP-UHFFFAOYSA-L disodium benzene-1,4-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=C(S([O-])(=O)=O)C=C1 PFVJLGPIYRQLHP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WKNIDMJWLWUOMZ-UHFFFAOYSA-N [K].[Cr] Chemical compound [K].[Cr] WKNIDMJWLWUOMZ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- LCIVMZVFUUKKII-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].[Na].[Na].C1=CC=CC=C1 LCIVMZVFUUKKII-UHFFFAOYSA-N 0.000 description 1
- WJAASTDRAAMYNK-UHFFFAOYSA-N benzyl carbamimidothioate;hydron;chloride Chemical compound Cl.NC(=N)SCC1=CC=CC=C1 WJAASTDRAAMYNK-UHFFFAOYSA-N 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- WITXPSHEXVRIHX-UHFFFAOYSA-K trisodium benzene-1,2,3-trisulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)c1cccc(c1S([O-])(=O)=O)S([O-])(=O)=O WITXPSHEXVRIHX-UHFFFAOYSA-K 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E05—LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
- E05B—LOCKS; ACCESSORIES THEREFOR; HANDCUFFS
- E05B9/00—Lock casings or latch-mechanism casings ; Fastening locks or fasteners or parts thereof to the wing
- E05B9/08—Fastening locks or fasteners or parts thereof, e.g. the casings of latch-bolt locks or cylinder locks to the wing
- E05B9/084—Fastening of lock cylinders, plugs or cores
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T70/00—Locks
- Y10T70/70—Operating mechanism
- Y10T70/7441—Key
- Y10T70/7486—Single key
- Y10T70/7508—Tumbler type
- Y10T70/7559—Cylinder type
- Y10T70/7661—Detachable or removable cylinder
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T70/00—Locks
- Y10T70/80—Parts, attachments, accessories and adjuncts
- Y10T70/8432—For key-operated mechanism
- Y10T70/8459—Housings
- Y10T70/8541—Mounting arrangements
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Closures For Containers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lock And Its Accessories (AREA)
Description
Framgangsmåte for framstilling av dialkalimetallsaltet av benzen-1 : 4- eller naftalen-2 : 6-disulfonsyrer, eller de tilsvarende frie disulfonsyrer. Process for the preparation of the dialkali metal salt of benzene-1:4- or naphthalene-2:6-disulfonic acids, or the corresponding free disulfonic acids.
Foreliggende oppfinnelse vedrører en The present invention relates to a
framgangsmåte for framstilling av dialkalimetallsaltet av benzen-1 : 4- eller naftalen-2 : 6-disulfonsyrer, eller de tilsvarende frie disulfonsyrer. process for the preparation of the dialkali metal salt of benzene-1:4- or naphthalene-2:6-disulfonic acids, or the corresponding free disulfonic acids.
Ved de hittil beskrevne framgangs-måter for disulfonering av benzen, er det In the hitherto described procedures for the disulfonation of benzene, it is
vanlige produkt benzen 1—3 disulfonsyre. common product benzene 1-3 disulfonic acid.
Når det arbeides ved høye temperaturer i When working at high temperatures i
svovelsyreoppløsning i nærvær av spesielle sulfuric acid solution in the presence of special
katalysatorer, får man bare et dårlig utbytte av benzen 1-4 disulfonsyre. (Behrend catalysts, only a poor yield of benzene 1-4 disulfonic acid is obtained. (Management
og Mertelsmann, Annalen 1911, 378, 352). and Mertelsmann, Annalen 1911, 378, 352).
I henhold til foreliggende oppfinnelse According to the present invention
tilveiebringes en framgangsmåte for framstilling av de ovenfor angitte substanser a procedure for the production of the above-mentioned substances is provided
ved at alkalimetallsaltet av den isomere in that the alkali metal salt of the isomeric
benzen-1 : 3- eller naftalen-2 : 7-disulfonsyre, opphetes til en temperatur fra 250 benzene-1:3- or naphthalene-2:7-disulfonic acid, heated to a temperature from 250
til 600° C, i nærvær av en katalysator om-fattende et tungmetall eller en tungmetall-forbindelse, f. eks. en forbindelse av kvikk-sølv eller krom, eller i fravær av en kata-; to 600° C, in the presence of a catalyst comprising a heavy metal or a heavy metal compound, e.g. a compound of mercury or chromium, or in the absence of a cata-;
lysator ved en temperatur innenfor området 375—600° C, fortrinnsvis i en inert lysator at a temperature within the range 375-600° C, preferably in an inert
atmosfære og om ønskes erholdes en fri atmosphere and, if desired, a free one is obtained
syre fra alkalimetallsaltet av den aromatiske disulfonsyre ved at dette bringes i acid from the alkali metal salt of the aromatic disulfonic acid by bringing this in
kontakt med en kjationutvekslerharpiks. contact with a cation exchange resin.
Opphetingen kan finne sted ved atmos-færisk trykk eller forhøyet trykk. Reak-sjonen finner fortrinnsvis sted i en inert The heating can take place at atmospheric pressure or elevated pressure. The reaction preferably takes place in an inert
atmosfære som kulldioksyd eller nitrogen, atmosphere such as carbon dioxide or nitrogen,
skjønt det ikke er av avgjørende betyd-ning at luft skal utelukkes, men når luft although it is not of decisive importance that air should be excluded, but when air
er tilstede, er det ønskelig at det bare er en is present, it is desirable that there is only one
begrenset adgang av luften til reaksjons-karet. limited access of the air to the reaction vessel.
Isomeriseringen vil finne sted i fravær av en katalysator ved en temperatur av 375° C eller høyere. Imidlertid foretrekkes det å utføre prosessen i nærvær av en katalysator, idet lavere arbeidstem-peraturer i så fall kan anvendes, dvs. temperaturer ned til 250° C. Vi har funnet at substanser som bare inneholder visse tunge metaller er meget skikket, særlig slike som inneholder kvikksølv og krom. I alle tilfelle er det ønskelig ikke å utføre prosessen ved temperaturer over ca. 600° C, da spaltning av de reagerende stoffer lett vil kunne inntre. The isomerization will take place in the absence of a catalyst at a temperature of 375°C or higher. However, it is preferred to carry out the process in the presence of a catalyst, as lower working temperatures can then be used, i.e. temperatures down to 250° C. We have found that substances which only contain certain heavy metals are very suitable, especially such as contains mercury and chromium. In all cases, it is desirable not to carry out the process at temperatures above approx. 600° C, as decomposition of the reacting substances will easily occur.
Kalium- og natriumsaltene av benzen-1 : 3-eller naftalen-2 : 7-disulfonsyrer har The potassium and sodium salts of benzene-1 : 3- or naphthalene-2 : 7-disulfonic acids have
vist seg særlig skikket som utgangsma-terialer, og av disse foretrekkes det å an-vende natriumsaltene, da i dette tilfelle utbyttet av de ønskete disulfonsyrer er noe høyere enn med kaliumsaltene, og omkost-ningene er lavere. proved particularly suitable as starting materials, and of these it is preferred to use the sodium salts, as in this case the yield of the desired disulfonic acids is somewhat higher than with the potassium salts, and the costs are lower.
Det er ofte hensiktsmessig å isolere produktene ved frigjøring av de frie disulfonsyrer i uren form. Produktene av det urene salt eller de frie syrer kan også omdannes til klorider ved reaksjon, f. eks. med fosforpentaklorid eller tionylklorid, eller til de tilsvarende sulfonamider ved reaksjon med f. eks. ammoniakk. It is often appropriate to isolate the products by releasing the free disulfonic acids in impure form. The products of the impure salt or the free acids can also be converted into chlorides by reaction, e.g. with phosphorus pentachloride or thionyl chloride, or to the corresponding sulphonamides by reaction with e.g. ammonia.
Foruten den fordel at det fåes den ønskete syre med store utbytter, oppnås den videre fordel under isoleringen av det ønskete produkt at det er mer hensiktsmessig å utskille den ønskete disulfonsyre fra utgangssyren når mengden av først-nevnte er høy. Besides the advantage that the desired acid is obtained with large yields, the further advantage is achieved during the isolation of the desired product that it is more appropriate to separate the desired disulfonic acid from the starting acid when the quantity of the first-mentioned is high.
Fremgangsmåten skal klargjøres ved følgende eksempler, hvor alle deler og pro-sentangivelser er etter vekt: The procedure must be clarified by the following examples, where all parts and percentages are by weight:
Eksempel 1. Example 1.
Det vannfrie dinatriumsalt av benzen-1 : 3-disulfonsyre (282 deler) ble blandet med kvikksølv-(II)-oksyd (43 deler), og blandingen ble opphetet i en atmosfære av kulldioksyd ved et trykk av 4 atm. i 6 timer ved 425° C. The anhydrous disodium salt of benzene-1:3-disulfonic acid (282 parts) was mixed with mercuric (II) oxide (43 parts) and the mixture was heated in an atmosphere of carbon dioxide at a pressure of 4 atm. for 6 hours at 425° C.
Produktet ble ekstrahert med vann, og de frie ekstrakter ble ført gjennom en ko-lonne av en aktivert kationutvekslerharpiks for å frigjøre den frie sulfonsyre, og utbyttet i uren form andro til 230 deler. Fra en aliquot del av dette produkt ble det fremstilt bis(S-benzyltiuronium)benzen-para-disulfonat (Smp. 247° C) i en mengde som viste at benzen-1 : 4-di^ulfonsyre fåes med et utbytte svarende til 52 pst. av det teoretiske. Produktet ble videre bestemt ved omdannelse til benzen-paradi-sulfonylklorid, som ved reaksjon med ammoniakk ga benzen-paradisulfonamid (Sm. 291° C). The product was extracted with water, and the free extracts were passed through a column of an activated cation exchange resin to liberate the free sulfonic acid, and the yield in crude form was 230 parts. From an aliquot part of this product, bis(S-benzylthiuronium)benzene-para-disulfonate (M.P. 247° C) was prepared in an amount which showed that benzene-1 : 4-disulfonic acid is obtained with a yield corresponding to 52 percent of the theoretical. The product was further determined by conversion to benzene paradisulfonyl chloride, which on reaction with ammonia gave benzene paradisulfonamide (M. 291° C).
Eksempel 2. Example 2.
Når det vannfrie dikaliumsalt av benzen-1 : 3-disulfonsyre (315 deler) ble behandlet ved fremgangsmåten etter eksempel 1, fikk man isolert 50 deler (9 pst. av den teoretiske mengde) av bis(S-benzyl-tiuronium)benzen-para-disulfonat. When the anhydrous dipotassium salt of benzene-1:3-disulfonic acid (315 parts) was treated by the method according to example 1, 50 parts (9 per cent of the theoretical amount) of bis(S-benzyl-thiuronium)benzene-para were isolated -disulfonate.
Eksempel 3. Example 3.
En blanding av dinatriumnaftalen-2 : 7-disulfonat (664 deler) og kvikksølv-(II)-oksyd (43,2 deler) ble innesluttet i en atmosfære av kulldioksyd og opphetet til 425° C i 6 timer. Etter avkjøling ble produktet ekstrahert med vann, og en aliquot del ble behandlet med en vandig oppløs-ning av S-benzyltiuroniumklorid, hvorved man fikk bis(S-benzyltiuronium)naftalen-2 : 6-disulfonat med et utbytte svarende til tilstedeværelsen av produktet av i det minste 15 pst. dinatriumnaftalen-2 : 6-disulfonat. A mixture of disodium naphthalene-2:7-disulfonate (664 parts) and mercuric (II) oxide (43.2 parts) was enclosed in an atmosphere of carbon dioxide and heated to 425°C for 6 hours. After cooling, the product was extracted with water, and an aliquot part was treated with an aqueous solution of S-benzylthiuronium chloride, whereby bis(S-benzylthiuronium)naphthalene-2:6-disulfonate was obtained with a yield corresponding to the presence of the product of at least 15 percent disodium naphthalene-2:6-disulfonate.
Smeltepunktet (271—274° C) og det infrarøde absorbsjonsspektrum av saltet var identisk med tallene for en autentisk prøve av bis(S-benzyltiuronium)naftalen-2 : 6-disulfonat. The melting point (271-274° C.) and the infrared absorption spectrum of the salt were identical to the figures for an authentic sample of bis(S-benzylthiuronium)naphthalene-2:6-disulfonate.
Naftalen-2 : 6-disulfonsyre ble lett erholdt i fri tilstand som en vandig opp-løsning ved å bringe natriumsaltoppløs-ningen i kontakt med en kationutvekslerharpiks i sur form. Naphthalene-2:6-disulfonic acid was readily obtained in the free state as an aqueous solution by contacting the sodium salt solution with a cation exchange resin in acidic form.
Eksempel 4. Example 4.
Når dinatriumnaftalen-2 : 7-disulfonat ble behandlet som i eksempel 3 under anvendelse av kadrnium-metallstøv (22 deler) i stedet for kvikksølv-(II)-oksyd, fikk man bis(S-benzyltiuronium)-naftalen-2 : 6-disulfonat med et utbytte svarende til tilstedeværelsen av 10 pst. av 2 : 6-disulfonatet i reaksjonsproduktet. When disodium naphthalene-2 : 7-disulfonate was treated as in Example 3 using cadmium metal dust (22 parts) instead of mercuric (II) oxide, bis(S-benzylthiuronium)-naphthalene-2 : 6- disulfonate with a yield corresponding to the presence of 10 percent of the 2:6-disulfonate in the reaction product.
Eksempel 5. Example 5.
Når dinatriumnaftalen-2:7-disulfonat alene ble opphetet som i eksempel 3, var utbyttet av bis(S-benzyltiuronium)-naftalen-2:6-disulfonat ekvivalent med tilstedeværelsen av 7 pst. av 2:6-disulfonatet i reaksjonsproduktet. Det samme utbytte ble erholdt når 41,4 deler av blypulver bie tilsatt til dinatriumsaltet og blandingen behandlet som i eksempel 3. When disodium naphthalene-2:7-disulfonate alone was heated as in Example 3, the yield of bis(S-benzylthiuronium)-naphthalene-2:6-disulfonate was equivalent to the presence of 7 percent of the 2:6-disulfonate in the reaction product. The same yield was obtained when 41.4 parts of lead powder were added to the disodium salt and the mixture treated as in Example 3.
Til sammeligning skal nevnes at når dinatriumbenzen-1:3-disulfonat (820 deler) ble opphetet i 24 timer ved 275° C i en atmosfære av kulldioksyd, var forbindelsen uforandret. For comparison, it should be mentioned that when disodium benzene-1:3-disulfonate (820 parts) was heated for 24 hours at 275° C. in an atmosphere of carbon dioxide, the compound was unchanged.
Eksempel 6. Example 6.
Dinatriumbenzen-1:3-disulfonat (800 deler) ble opphetet i 12 timer ved 425° C i en atmosfære av kulldioksyd. Man fikk 720 deler av et produkt hvis sammensetning var dinatriumbenzen-p-disulfonat (70—75 pst.), dinatriumbenzen-m-disulfonat (ca. Disodium benzene 1:3-disulfonate (800 parts) was heated for 12 hours at 425°C in an atmosphere of carbon dioxide. 720 parts of a product were obtained whose composition was disodium benzene p-disulphonate (70-75 per cent), disodium benzene m-disulphonate (approx.
5 pst.), trinatriumbenzen-l:3:5-trisulfonat (ca. 20 pst.) og natriumsulfat ca. 1—3 pst.) 5 per cent), trisodium benzene-1:3:5-trisulfonate (approx. 20 per cent) and sodium sulphate approx. 1-3 per cent.)
Eksempel 7. Example 7.
Dinatriumbenzen-1:3-disulfonat (820 deler) ble blandet intimt med kalium-krom-alun (57 deler), og blandingen ble derpå opphetet i 24 timer ved 275° C i en atmosfære av kulldioksyd. Produktet veiet 640 deler, inneholdende ca. 85 pst. av dinatriumbenzen-p-disulfonat og ca. 15 pst. trinatriumbenzen-trisulfonat. Produktets sammensetning ble bestemt ved infrarød analyse. Disodium benzene 1:3-disulfonate (820 parts) was intimately mixed with potassium chromium alum (57 parts) and the mixture was then heated for 24 hours at 275°C in a carbon dioxide atmosphere. The product weighed 640 parts, containing approx. 85 percent of disodium benzene-p-disulfonate and approx. 15 percent trisodium benzene trisulfonate. The composition of the product was determined by infrared analysis.
Eksempel 8. Example 8.
Dinatriumbenzen-1:3-disulfonat (820 deler) ble blandet med kvikksølv-(II)-oksyd Disodium benzene 1:3-disulfonate (820 parts) was mixed with mercuric (II) oxide
(43 deler), og blandingen ble derpå behandlet som i eksempel 7. Produktet (760 deler) var dinatriumbenzen-1:4-disulfonat, som inneholdt ca, 5 pst. m-disulfonat og ca. 10 pst. trisulfonat, hvilket ble bestemt ved infrarød analyse. (43 parts), and the mixture was then treated as in Example 7. The product (760 parts) was disodium benzene-1:4-disulfonate, containing about 5 percent m-disulfonate and about 10 percent trisulfonate, which was determined by infrared analysis.
Eksempel 9. Example 9.
Dinatriumbenzen-m-disulf onat (500 deler) og kvikksølv(II)-sulfat (60 deler) ble blandet intimt, og blandingen ble opphetet i en nitrogen-atmosfære i 6 timer ved 425° C. Produktet ble opparbeidet som i de foran anførte eksempler, og man fikk 450 deler av dinatriumbenzen-1:4-disulfonat, som inneholdt en liten mengde av trinatriumbenzen-1:3:5-trisulfonat. Disodium benzene m-disulfonate (500 parts) and mercuric (II) sulfate (60 parts) were intimately mixed, and the mixture was heated in a nitrogen atmosphere for 6 hours at 425° C. The product was worked up as in the above examples, and 450 parts of disodium benzene 1:4-disulfonate were obtained, which contained a small amount of trisodium benzene 1:3:5-trisulfonate.
Syrer som fåes ved fremgangsmåten ifølge oppfinnelsen kan omdannes videre ved passende fremgangsmåter til høymole-kylære polymerer, eller omdannes til teref-talsyre eller et derivat som f. eks. tereftal-onitril, f. eks. ved de fremgangsmåter som er bekrevet i: H. Schiff Ber. 1876, 9, 581 (benzendi- sulfonat). R. Ebert and V. Merz, Ber. 1876, 9, 592 (naf talendisulfonat). Acids obtained by the method according to the invention can be further converted by suitable methods into high-molecular polymers, or converted into terephthalic acid or a derivative such as e.g. terephthalonitrile, e.g. by the methods described in: H. Schiff Ber. 1876, 9, 581 (benzenedi- sulfonate). R. Ebert and V. Merz, Ber. 1876, 9, 592 (naphthalene disulfonate).
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI662651A FI45683C (en) | 1966-10-08 | 1966-10-08 | Fastening device for fastening a cylinder lock locking cylinder in a lock housing. |
Publications (1)
Publication Number | Publication Date |
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NO125153B true NO125153B (en) | 1972-07-24 |
Family
ID=8507382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO169958A NO125153B (en) | 1966-10-08 | 1967-10-03 |
Country Status (6)
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US (1) | US3501933A (en) |
DE (1) | DE1678063A1 (en) |
DK (1) | DK119497B (en) |
FI (1) | FI45683C (en) |
NO (1) | NO125153B (en) |
SE (1) | SE334309B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3863475A (en) * | 1974-02-07 | 1975-02-04 | Victor Comptometer Corp | Function Control Key Locks |
US4441347A (en) * | 1981-06-08 | 1984-04-10 | Taylor James L | Lock assembly with interchangeable noses for safe deposit boxes |
DE19849179C1 (en) * | 1998-10-24 | 2000-03-23 | Raymond A & Cie | Bracket for vehicle door lock casing has ring to fit behind shoulder on lock casing and axially extending support arms |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2093038A (en) * | 1935-03-28 | 1937-09-14 | Kingston Products Corp | Mounting means |
US2061978A (en) * | 1935-05-22 | 1936-11-24 | Pentka Joseph | Electrically operated lock for motor vehicles |
-
1966
- 1966-10-08 FI FI662651A patent/FI45683C/en active
-
1967
- 1967-10-03 NO NO169958A patent/NO125153B/no unknown
- 1967-10-03 SE SE13562/67A patent/SE334309B/xx unknown
- 1967-10-04 DE DE19671678063 patent/DE1678063A1/en active Pending
- 1967-10-05 DK DK496567AA patent/DK119497B/en unknown
- 1967-10-06 US US673468A patent/US3501933A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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DK119497B (en) | 1971-01-11 |
US3501933A (en) | 1970-03-24 |
FI45683B (en) | 1972-05-02 |
FI45683C (en) | 1972-08-10 |
DE1678063A1 (en) | 1971-08-12 |
SE334309B (en) | 1971-04-19 |
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