NO167098B - MODULAR PROTECTION STRUCTURE FOR UNDERWATER INSTALLATIONS. - Google Patents
MODULAR PROTECTION STRUCTURE FOR UNDERWATER INSTALLATIONS. Download PDFInfo
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- NO167098B NO167098B NO885110A NO885110A NO167098B NO 167098 B NO167098 B NO 167098B NO 885110 A NO885110 A NO 885110A NO 885110 A NO885110 A NO 885110A NO 167098 B NO167098 B NO 167098B
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- Norway
- Prior art keywords
- alkali metal
- ampicillin
- aminobenzylpenicillin
- methylene chloride
- solution
- Prior art date
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- -1 alkali metal salts Chemical class 0.000 claims description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 229960000723 ampicillin Drugs 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Substances [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- 125000005270 trialkylamine group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical class [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=CC=C1 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 1
- 229960003311 ampicillin trihydrate Drugs 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- E21B33/00—Sealing or packing boreholes or wells
- E21B33/02—Surface sealing or packing
- E21B33/03—Well heads; Setting-up thereof
- E21B33/035—Well heads; Setting-up thereof specially adapted for underwater installations
- E21B33/037—Protective housings therefor
Landscapes
- Geology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mining & Mineral Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Fluid Mechanics (AREA)
- Physics & Mathematics (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Toys (AREA)
- Laying Of Electric Cables Or Lines Outside (AREA)
- Helmets And Other Head Coverings (AREA)
- Revetment (AREA)
- Artificial Fish Reefs (AREA)
Description
Foreliggende oppfinnelse vedrører fremstilling av alkalimetallsalter av a-aminobenzylpenicillin. The present invention relates to the production of alkali metal salts of α-aminobenzylpenicillin.
a-aminobenzylpenicillin og dens epimerer, α-aminobenzylpenicillin and its epimers,
6-[ D (-)-a-aminofenylacetamido]penicillansyre og 6-[L(+)-a-aminofenylacetamido]penicillansyre, og salter herav er beskrevet i. US-patentskrift nr. 2.985.648 og delvis i norsk patentskrift nr. 115.737. Disse penicilliner er i be-sittelse av verdifull antibiotisk aktivitet og er nyttige som terapeutiske midler for dyr, innbefattet mennesker, ved behandling særlig av infeksjonssykdommer som forårsakes av Gram-positive og Gram-negative bakterier.. 6-[ D (-)-α-aminophenylacetamido]penicillanic acid and 6-[L(+)-α-aminophenylacetamido]penicillanic acid, and salts thereof are described in US patent no. 2,985,648 and partly in Norwegian patent no. 115,737. These penicillins possess valuable antibiotic activity and are useful as therapeutic agents for animals, including humans, in the treatment especially of infectious diseases caused by Gram-positive and Gram-negative bacteria.
a-aminobenzylpenicilliner foreligger normalt i form α-aminobenzylpenicillins are normally available in the form
av den frie syre, eller for å være mer nøyaktig som zwitterioner. Disse former er imidlertid, selv om de er egnet for oral admini-strering, for sparsomt oppløselig i vann til å kunne brukes på en hensiktsmessig måte som injiserbare preparater, og følgelig fremstilles injiserbare a-aminobenzylpenicilliner i form av alkalimetallsaltene som er lett oppløselig i vann. of the free acid, or to be more precise as zwitterions. However, these forms, although suitable for oral administration, are too sparingly soluble in water to be used appropriately as injectable preparations, and consequently injectable α-aminobenzylpenicillins are prepared in the form of the alkali metal salts which are readily soluble in water .
Tysk utlegningsskrift nr. 1.197.460 beskriver en fremgangsmåte for fremstilling av meget rene alkalimetallsalter av a-aminobenzylpenicillin (ampicillin). Man omsetter ampicillin i et organisk løsningsmiddel med trialkylamin til det tilsvarende løselige trialkylaminsalt og utfeller dette med et alkalimetallsalt av en karboksylsyre som alkalimetallsalt fra løsningen. German specification no. 1,197,460 describes a process for the production of very pure alkali metal salts of α-aminobenzylpenicillin (ampicillin). One converts ampicillin in an organic solvent with trialkylamine to the corresponding soluble trialkylamine salt and precipitates this with an alkali metal salt of a carboxylic acid as an alkali metal salt from the solution.
Tysk utlegningsskrift nr. 1.178.434 beskriver en tilsvarende fremgangsmåte for adskillelse av a-aminobenzylpenicillin og 6-aminopenicillansyre. Ampicillinet utvinnes imidlertid ikke som alkalimetallsalt, men som trialkylaminsalt. German specification no. 1,178,434 describes a similar method for separating α-aminobenzylpenicillin and 6-aminopenicillanic acid. However, the ampicillin is not recovered as an alkali metal salt, but as a trialkylamine salt.
Ved disse kjente fremgangsmåter er det nødvendig med et stort overskudd av trialkylamin for å løse ampicillinet som amipicillin-trialkylaminsalt. Således utgjør i henhold til tysk utlegningsskrift nr. 1.197.460 molforholdet trietylamin/ampicillin f.eks. 1,5-1,97. Det ble nå overraskende fastslått at ved anvendelse av dietylamin i metylenklorid følger fullstendig oppløs-ning av ampicillinet med et vesentlig lavere overskudd (12% i motsetning til minst 50% i henhold til teknikkens stand) og i løpet av meget kortere tid. In these known methods, a large excess of trialkylamine is required to dissolve the ampicillin as ampicillin-trialkylamine salt. Thus, according to German explanatory document no. 1,197,460, the molar ratio of triethylamine/ampicillin e.g. 1.5-1.97. It was now surprisingly established that when using diethylamine in methylene chloride, complete dissolution of the ampicillin follows with a significantly lower excess (12% as opposed to at least 50% according to the state of the art) and within a much shorter time.
Fremgangsmåten i henhold til foreliggende oppfinnelse for fremstilling av alkalimetallsalter a<y> a-aminobenzylpenicillin og dets epimerer ved omsetning av a-aminobenzylpenicillin med et amin i metylenklorid, filtrering av den oppnådde løsning og omsetning av filtratet med en alkalimetallforbindelse som er opp-løst i et organisk løsningsmiddel, er karakterisert ved at man som amin anvender dietylamin og som fellingsmiddel et alkalimetallmetoksyd, -jodid, -fenoksyd, -tiocyanat eller natriumsalt av etylacetoacetatet. The method according to the present invention for the production of alkali metal salts α-aminobenzylpenicillin and its epimers by reacting α-aminobenzylpenicillin with an amine in methylene chloride, filtering the solution obtained and reacting the filtrate with an alkali metal compound which is dissolved in an organic solvent, is characterized by using diethylamine as the amine and an alkali metal methoxide, iodide, phenoxide, thiocyanate or sodium salt of the ethyl acetoacetate as the precipitating agent.
Da dietylaminsaltet av a-aminobenzylpenicillin er godt oppløselig i de forskjelligste organiske løsningsmidler, så som metylenklorid, kloroform, nitroetan, acetonitril og tetra-kloretan, mens derimot alkalimetallsaltene er uoppløselig i disse, kan man bringe a-aminobenzylpenicillin i løsning under tilsetning av et moderat overskudd av dietylamin i metylenklorid og deretter utvinne f.eks. natriumsaltet ved tilsetning av et fellingsmiddel. As the diethylamine salt of a-aminobenzylpenicillin is well soluble in a wide variety of organic solvents, such as methylene chloride, chloroform, nitroethane, acetonitrile and tetrachloroethane, while the alkali metal salts are insoluble in these, one can bring a-aminobenzylpenicillin into solution by adding a moderate excess of diethylamine in methylene chloride and then recover e.g. the sodium salt by adding a precipitating agent.
Ved fremgangsmåten i henhold til oppfinnelse:n er temperaturområdet som ampicillin-dietylaminsaltet fremstilles i, ikke så kritisk som ved anvendelse av trietylamin. Penicillinet omsettes med dietylaminet ved romtemperatur, mens omsetningen med trietylamin må foregå ved en temperatur på 0°C (kfr. tysk utlegningsskrift nr. 1.19 7.460). En videre økonomisk fordel ved fremgangsmåten i henhold til foreliggende oppfinnelse ligger i anvendelse av alkalimetallmetoksyd, -jodid, -fenoksyd eller -tiocyanat eller natriumsaltet av etylacetoacetatet som fellingsmiddel. Natrium-metoksyd og -jodid er lett tilgjengelige og billige forbindelser. Dessuten får man derved bedre filtrerbare ampicillin-natriumsalter enn med det tradisjonelle fellingsmiddel. In the method according to the invention, the temperature range in which the ampicillin-diethylamine salt is produced is not as critical as when triethylamine is used. Penicillin reacts with diethylamine at room temperature, while the reaction with triethylamine must take place at a temperature of 0°C (cf. German explanatory document no. 1.19 7.460). A further economic advantage of the method according to the present invention lies in the use of alkali metal methoxide, iodide, phenoxide or thiocyanate or the sodium salt of the ethyl acetoacetate as precipitating agent. Sodium methoxide and iodide are readily available and cheap compounds. In addition, this results in better filterable ampicillin sodium salts than with the traditional precipitating agent.
a-aminobenzylpenicillinet kan ved fremgangsmåten i henhold til oppfinnelsen anvendes i enhver lett tilgjengelig form. Ved anvendelse av trihydratet tilsettes- den innledningsvis fremstilte blanding med dietylaminet i metylenklorid også et avvanningsmiddel, f.eks. vannfritt natrium- eller kaliumsulfat. Dette avvanningsmiddel fjernes deretter før utfellingen av alkali- The α-aminobenzylpenicillin can be used in the method according to the invention in any readily available form. When using the trihydrate, a dehydrating agent, e.g. anhydrous sodium or potassium sulfate. This dewatering agent is then removed before the precipitation of alkali
metallsaltet fra løsningen. the metal salt from the solution.
Oppfinnelsen skal i det følgende beskrives ved hjelp av eksempler, hvorved trivialnavnet "ampicillin" anvendes for a-aminobenzylpenicillinet. In the following, the invention will be described with the help of examples, whereby the trivial name "ampicillin" is used for the α-aminobenzylpenicillin.
Eksempel 1 Example 1
50 g ampicillin (aktiv vekt) finmales og oppslemmes i 500 ml metylenklorid. Deretter tilsettes 17 ml dietylamin (overskudd: 12%) dråpevis i løpet av 15 minutter, og blandingen røres i ytterligere 45 minutter. Løsningen filtreres så, og en løsning av 21,4 g natriumjodid i 110 ml isopropanol tilsettes under røring i løpet av 15 minutter. Denne løsning røres til be-gynnende utfelling og får så henstå i 2 timer ved romtemperatur. Natriumsaltet av ampicillin som danner seg, filtreres av og tørkes i vakuumtørkeskap ved 40°C til konstant vekt. 50 g of ampicillin (active weight) is finely ground and slurried in 500 ml methylene chloride. Then 17 ml of diethylamine (excess: 12%) is added dropwise over 15 minutes, and the mixture stir for a further 45 minutes. The solution is then filtered, and a solution of 21.4 g of sodium iodide in 110 ml of isopropanol is added with stirring over 15 minutes. This solution is stirred until precipitation begins and is then allowed to stand for 2 hours at room temperature. The sodium salt of ampicillin that forms is filtered off and dried in a vacuum oven at 40°C to constant weight.
Ved ytterligere forsøk anvendes istedenfor natrium-jodidløsningen a) en løsning av 7,8 g natrium-metoksyd i 100 ml isopropanol og 50 ml metylenklorid, b) en løsning av 16,5 g natriumfenoksyd i 100 ml isopropanol, samt c) 1 ekvivalent natriumsalt av etylacetoacetatet pr. mol ampicillin, oppløst i isopropanol. In further experiments, instead of the sodium iodide solution, a) a solution of 7.8 g sodium methoxide in 100 ml isopropanol and 50 ml methylene chloride is used, b) a solution of 16.5 g sodium phenoxide in 100 ml isopropanol, and c) 1 equivalent sodium salt of the ethyl acetoacetate per mol of ampicillin, dissolved in isopropanol.
Eksempel 2 Example 2
59 g ampicillintrihydrat med en renhetsgrad på 85,3%, samt 50 g vannfritt natriumsulfat suspenderes i 500 ml metylenklorid. Til denne blanding tilsettes i løpet av 30 minutter under god røring 22,1 ml dietylamin. Etter at man har rørt ytterligere 30 minutter, filtreres blandingen. Til denne løsning tilsettes 50 g vannfritt kalsiumsulfat, suspensjonen røres i ca. 45 minutter og filtreres på nytt. Til den således oppnådde løs-ning tilsettes i løpet av 40 minutter ved en temperatur på 26°C under god røring 9,0 g natrium-metoksyd, oppløst i 200 ml isopropanol og 200 ml metylenklorid. Krystalliseringen begynner ganske spontant, og man fortsetter røringen i 3 timer til. Det salt som har dannet seg, filtreres fra, vaskes 2 ganger med 60 respektive 40 ml metylenklorid og tørkes ca. 14 timer ved 40 oC. 59 g of ampicillin trihydrate with a degree of purity of 85.3%, as well as 50 g of anhydrous sodium sulfate are suspended in 500 ml of methylene chloride. 22.1 ml of diethylamine is added to this mixture over the course of 30 minutes with good stirring. After stirring for a further 30 minutes, the mixture is filtered. 50 g of anhydrous calcium sulphate is added to this solution, the suspension is stirred for approx. 45 minutes and filtered again. To the solution thus obtained, 9.0 g of sodium methoxide, dissolved in 200 ml of isopropanol and 200 ml of methylene chloride, are added over the course of 40 minutes at a temperature of 26°C with good stirring. Crystallization begins quite spontaneously, and the stirring is continued for another 3 hours. The salt that has formed is filtered off, washed twice with 60 and 40 ml of methylene chloride, respectively, and dried for approx. 14 hours at 40 oC.
Eksempel 3 Example 3
51 ml dietylamin tilsettes ved romtemperatur langsomt til en omrørt oppslemming av 150 g fint fordelt, vannfritt ampicillin (aktiv vekt) i 160 ml tørt metylenklorid. Etter oppløs-ningen filtreres løsningen over et bakteriologisk filter ned i en ren, tørr og steril beholder. Samtidig oppløses 22,4 g natrium-metoksyd i et rent og tørt kar i en omrørt blanding av 350 ml metylenklorid og 350 ml isopropanol. En restblakking fjernes ved filtrering under sterile betingelser. Deretter tilsettes dette filtrat i løpet av 30 minutter i nærvær av podekrystaller langsomt til den omrørte løsning av ampicillinet. Etter ca. 3 timer fraskilles det utfelte natriumsalt under utelukkelse av fuktighet og vaskes med metylenklorid. Så hurtig som mulig blir det over-ført til et tørkeskap med luftsirkulasjon og tørkes i 6 timer ved 40°C, til fuktighetsinnholdet utgjør mindre enn 1,5%. 51 ml of diethylamine is added slowly at room temperature to a stirred slurry of 150 g of finely divided, anhydrous ampicillin (active weight) in 160 ml of dry methylene chloride. After dissolution, the solution is filtered over a bacteriological filter into a clean, dry and sterile container. At the same time, 22.4 g of sodium methoxide are dissolved in a clean and dry vessel in a stirred mixture of 350 ml of methylene chloride and 350 ml of isopropanol. A residual precipitate is removed by filtration under sterile conditions. This filtrate is then added slowly over the course of 30 minutes in the presence of seed crystals to the stirred solution of the ampicillin. After approx. After 3 hours, the precipitated sodium salt is separated while excluding moisture and washed with methylene chloride. As quickly as possible, it is transferred to a drying cabinet with air circulation and dried for 6 hours at 40°C, until the moisture content is less than 1.5%.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO885110A NO167098C (en) | 1988-11-16 | 1988-11-16 | MODULAR PROTECTION STRUCTURE FOR UNDERWATER INSTALLATIONS. |
| GB8925792A GB2226352B (en) | 1988-11-16 | 1989-11-15 | Protective structure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO885110A NO167098C (en) | 1988-11-16 | 1988-11-16 | MODULAR PROTECTION STRUCTURE FOR UNDERWATER INSTALLATIONS. |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO885110D0 NO885110D0 (en) | 1988-11-16 |
| NO885110L NO885110L (en) | 1990-05-18 |
| NO167098B true NO167098B (en) | 1991-06-24 |
| NO167098C NO167098C (en) | 1991-10-02 |
Family
ID=19891436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO885110A NO167098C (en) | 1988-11-16 | 1988-11-16 | MODULAR PROTECTION STRUCTURE FOR UNDERWATER INSTALLATIONS. |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB2226352B (en) |
| NO (1) | NO167098C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO166012C (en) * | 1988-10-14 | 1991-05-15 | Norske Stats Oljeselskap | PROTECTION DEVICE. |
| GB2234002A (en) * | 1989-06-16 | 1991-01-23 | Northern Ocean Services Ltd | Protective structure for sub-sea well heads or Xmas trees |
| US5259458A (en) * | 1991-09-19 | 1993-11-09 | Schaefer Jr Louis E | Subsea shelter and system for installation |
| NO940607L (en) * | 1994-02-22 | 1995-08-23 | Kongsberg Offshore As | Protective device for a device mounted on the seabed |
| GB2287053B (en) * | 1994-03-02 | 1997-07-16 | Stena Offshore Ltd | Dropped object protection for subsea installations |
| NO20015649L (en) * | 2001-11-20 | 2003-05-21 | Abb Offshore Systems As | Protective structure for underwater installations |
| NO333245B1 (en) * | 2011-04-07 | 2013-04-15 | Oilfield Technology Group As | Device for operations in an underwater installation |
| NO341496B1 (en) | 2014-01-03 | 2017-11-27 | Subsea Logistics As | Submarine storage device and system, and method |
| CN104085518A (en) * | 2014-07-29 | 2014-10-08 | 中国海洋石油总公司 | Cover plate with underwater robot interface |
| EP3841278B1 (en) * | 2018-08-20 | 2024-04-17 | Csub As | Subsea well protection assembly |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1367200A (en) * | 1971-11-02 | 1974-09-18 | Oceaneering Int Inc | Apparatus for protecting underwater equipment |
| US4239417A (en) * | 1977-11-23 | 1980-12-16 | A/S Hoyer-Ellefsen, Ing. T. Furuholmen A/S | Multi-purpose marine structure |
| GB1602001A (en) * | 1978-02-20 | 1981-11-04 | Fmc Corp | Apparatus for protection of subsea structures |
| US4220421A (en) * | 1978-11-27 | 1980-09-02 | Fmc Corporation | Subsea wellhead protective enclosure |
| AU5669986A (en) * | 1986-03-17 | 1987-10-09 | William J. Dore | Artificial reef |
-
1988
- 1988-11-16 NO NO885110A patent/NO167098C/en unknown
-
1989
- 1989-11-15 GB GB8925792A patent/GB2226352B/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO885110D0 (en) | 1988-11-16 |
| GB2226352A (en) | 1990-06-27 |
| GB2226352B (en) | 1992-12-16 |
| NO885110L (en) | 1990-05-18 |
| GB8925792D0 (en) | 1990-01-04 |
| NO167098C (en) | 1991-10-02 |
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