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Showing posts with label 2-(3-Nitrophenyl)-1. Show all posts
Showing posts with label 2-(3-Nitrophenyl)-1. Show all posts

Thursday 18 June 2015

2-(3-Nitrophenyl)-1,3-dioxolane


9

2-(3-Nitrophenyl)-1,3-dioxolane [6952-67-6]

1H-NMR


1H NMR
1H-NMR: 2-(3-Nitrophenyl)-1,3-dioxolane
250 MHz, CDCl3
interactive spectrum
delta [ppm]mult.atomsassignment
4.05-4.18m4 H-OCH2CH2O-
5.90s1 HO-CH-O
7.54-7.60m1 H5-H
7.79-7.83m1 H6-H
8.20-8.25m1 H4-H
8.35-8.37m1 H2-H
7.26CHCl3
10.15s1 HCHO (educt)

ChemSpider 2D Image | 2-(3-Nitrophenyl)-1,3-dioxolane | C9H9NO4

13C-NMR

13C NMR

13C-NMR: 2-(3-Nitrophenyl)-1,3-dioxolane
250 MHz, CDCl3
interactive spectrum
delta [ppm]assignment
65.5-OCH2CH2O-
102.3-O-CH-O-
121.7C2
124.0C4
129.4C5
132.7C6
140.4C1
148.3C3
76.5-77.5CDCl3

IR

IR

IR: 2-(3-Nitrophenyl)-1,3-dioxolane
[KBr, T%, cm-1]
[cm-1]assignment
3093arom. C-H valence
2978aliph. C-H valence
2905, 2862C-H valence
2769C-H valence, O-CH-O
1621, 1588arom. C=C valence
1532, 1359N=O valence
1532, 1359N=O valence

Acid catalyzed acetalisation of 3-nitrobenzaldehyde with ethanediol to the correspondent 1,3-dioxolane

3-Nitrobenzaldehyde+1,2-Ethanediol
4-toluenesulfonic
acid
reacts to
2-(3-Nitrophenyl)-1,3-dioxolane+Water; Side reactions

Acid catalyzed acetalisation of 3-nitrobenzaldehyde with ethanediol to the correspondent 1,3-dioxolane

Operating scheme

Operating scheme
Reaction type:reaction of the carbonyl group in aldehydes, acetalisation
Substance classes:aldehyde, acetal, alcohol, protecting group, acid catalyst
Techniques:removal of water by azeotropic distillation, heating under reflux with Soxhlet extractor (for 10 mmol preparation), stirring with magnetic stir bar, evaporating with rotary evaporator, shaking out, extracting, recrystallizing, filtering, heating with oil bath
Batch scale:0.1 mol0.01 mol3-Nitrobenzaldehyde

Reaction

3-Nitrobenzaldehyde (15.1 g, 100 mmol), ethanediole (6.83 g, 6.20 mL, 110 mmol) and 4-toluenesulfonic acid monohydrate (1.00 g, 5.30 mmol) exclamation are dissolved in cyclohexane (200 mL) in a dry 500 mL round bottom flask equipped with magnetic stirring bar, Dean Stark trap and reflux condenser. The reaction mixture is refluxed until no more water heureka is collected in the Dean-Stark trap (approx. 2-3 h exclamation ).

Work up

The hot reaction mixture is poured into another 500 mL round bottom flask to separate it from an oily sediment (800 mg) which has formed at the bottom of the reaction vessel. The sediment consists predominantly of product, starting material and 4-toluenesulfonic acid (1H-NMR spectrum). The solvent of the decanted solution is directly removed with a rotary evaporator exclamation. A yellow crystalline solid remains as crude product.
Crude product yield: 19.7 g; melting point 50-52 °C; Purity according to GC: 95% acetale + 4% aldehyde
In order to remove unreacted aldehyde as hydrogensulfite adduct, the crude product is dissolved in 200 mL tert-butyl methyl ether and extracted once with 20 mL saturated aqueous sodium hydrogen sulfite solution. The organic phase is dried over sodium sulfate, the sodium sulfate is removed by filtration and the solvent is evaporated with a rotary evaporator exclamation to yield a nearly colorless crystalline residue.
Yield: 17.9 g; melting point 57-58 °C; Purity according to GC: more than 99%.
The product is for most uses pure enough. If further purification is required, recrystallization from a solvent mixture of cyclohexane / tert-butyl methyl ether in a ratio of 1:1 (approximately 45 mL) can be carried out. The solution should be allowed to stand covered at room temperature until crystals form (if needed 1 to 2 days). If the solution is cooled quickly in an ice bath, only an oil generally forms. After cooling for a short time in an ice bath, the crystals are filtered and dried until constant mass is achieved in a desiccator at reduced pressure.
Yield: 15.9 g; melting point 57-58 °C; colorless crystals; purity according to GC: more than 99%.
The product can also be recrystallized from a small amount of hot ethanol, however with a much poorer yield.

Duration of the experiment

Approximately 5 hours including work up.

Where can I stop the experiment?

After evaporation of the cyclohexane from the reaction solution.

Recycling

The cyclohexane from the reaction mixture and the tert-butyl methylether are collected and redistilled.

Suggestions for waste disposal

WasteDisposal
aqueous phase from water separatorsolvent water mixtures, halogen free
aqueous phase from shaking outsolvent water mixtures, halogen free
dissolve residue from reaction flask in a small amount of acetoneorganic solvents, halogen free
mother liquor from recrystallisationorganic solvents, halogen free
sodium sulfatesolid waste, free from mercury

Substances required

Batch scale:0.1 mol0.01 mol3-Nitrobenzaldehyde
EductsAmountRiskSafety
3-Nitrobenzaldehyde
GHS07GHS09Warning
15.1 gH302 H411P273
1,2-Ethanediol
GHS07Warning
6.83 gH302P301 + 312
CatalystAmountRiskSafety
4-Toluenesulfonic acid monohydrate
GHS07Warning
0.19 gH315 H319 H335P261 P305 + 351 + 338
SolventsAmountRiskSafety
Cyclohexane
GHS02GHS08GHS07GHS09Danger
~ 230 mLH225 H304 H315 H336 H410P210 P233 P240 P273 P301 + 310 P302 + 352 P331 P403 + 235
tert-Butyl methyl ether
GHS02GHS07Danger
230 mLH225 H315P210
OthersAmountRiskSafety
Sodium disulfite
GHS05GHS07Danger
~ 13 gH302 H318 EUH031P280 P305 + 351 + 338 P313
Sodium sulfate
Danger
~ 5 g
Molecular sieve 4A
GHS07Warning
0 gH315 H319 H335P261 P305 + 351 + 338
Solvents for analysisAmountRiskSafety
tert-Butyl methyl ether
GHS02GHS07Danger
5 mLH225 H315P210

Substances produced

Batch scale:0.1 mol0.01 mol3-Nitrobenzaldehyde
ProductsAmountRiskSafety
2-(3-Nitrophenyl)-1,3-dioxolane
17.9 g
Water
H- EUH-P-

Equipment

Batch scale:0.1 mol0.01 mol3-Nitrobenzaldehyde
round bottom flask 100 mLround bottom flask 100 mLSoxhlet extractor 30 mLSoxhlet extractor 30 mL
extraction coneextraction conereflux condenserreflux condenser
heatable magnetic stirrer with magnetic stir barheatable magnetic stirrer with magnetic stir barseparating funnelseparating funnel
rotary evaporatorrotary evaporatorsuction flasksuction flask
Hirsch funnelHirsch funnelexsiccator with drying agentexsiccator with drying agent
oil bathoil bath
WasteDisposal
aqueous phase from water separatorsolvent water mixtures, halogen free
aqueous phase from shaking outsolvent water mixtures, halogen free
dissolve residue from reaction flask in a small amount of acetoneorganic solvents, halogen free
mother liquor from recrystallisationorganic solvents, halogen free
sodium sulfatesolid waste, free from mercury

Simple evaluation indices

Batch scale:0.1 mol0.01 mol3-Nitrobenzaldehyde
Atom economy91.5%
Yield93%
Target product mass1.82g
Sum of input masses74g
Mass efficiency24mg/g
Mass index41g input / g product
E factor40g waste / g product
Energy input870kJ
Energy efficiency

 

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Evaluation text

The classical variant of the "Acid catalyzed acetalisation of 3-nitrobenzaldehyde with ethanediol to the correspondent 1,3-dioxolane" is an easily performed experiment. The desired product is obtained in high yield question and high selectivity. Also the purity of the end product is very high.The mass efficiency is high to medium, compared to the other NOP experiments and thus evaluates as good question. The energy efficiency of the classical experiment is highly dependent on the method of heating question .
(Eco)toxicological data for the educt 3-nitrobenzaldehyde are incomplete, toxicological data for the product 2-(3-nitrophenyl)-1,3-dioxolane have not been determined at all. According to theoretical prediction methods both product and educt are suspected to have mutagenic, carcinogenic and sensitizing properties. The organic solvents used in this experiment ethanol,cyclohexane and tert-butyl methyl ether exhibit relatively low acute toxicity. Also the inorganic auxiliary materials do not pose significant dangers to human health question.
Educt, product and the solvents cyclohexane and tert-butyl methyl ether are biologically not easily degradable, and some are classified as dangerous to the environment because of their toxicity to aquatic organisms question .
Summed up we evaluate this experiment with a good economic efficiency and acceptable toxicological risks, but a relatively high environmental persistence of the used substances with the "yellow light".

Chromatogram

crude product chromatogram
GC: crude product
columnZebron ZB-1, L=15 m, d=0.25 mm, film 0.25 µm (Phenomenex)
inletinjector: 250°C, split injection, 0.15 µL
carrier gasHe, pre-column pressure 101 kPa
oven85°C (0 min), 8°C/min --> 250°C (10 min)
detectorFID, 250°C, H2 33.9 mL/min, synth. air 322 mL/min, isocratic N2, 15 mL/min (59 kPa)
integrationpercent concentration calculated from relative peak area

pure product chromatogram
GC: pure product
columnZebron ZB-1, L=15 m, d=0.25 mm, film 0.25 µm (Phenomenex)
inletinjector: 250°C, split injection, 0.15 µL
carrier gasHe, pre-column pressure 101 kPa
oven85°C (0 min), 8°C/min --> 250° C (10 min)
detectorFID 250°C, H2 33.9 mL/min, synth. air 322 mL/min, isocratic N2, flow 15 mL/min (59 kPa)
integrationpercent concentration calculated from relative peak area

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Bali indonesian food


Balinese cuisine - Wikipedia, the free encyclopedia

https://en.wikipedia.org/wiki/Balinese_cuisine
Balinese foods include lawar (chopped coconut, garlic, chilli, with pork or chicken meat and blood), Bebek betutu (duck stuffed with spices, wrapped in banana leaves and coconut husks cooked in a pit of embers), Balinese sate known as sate lilit made from spiced mince pressed onto skewers which are often lemon grass ...
Rice - ‎Spices and seasonings - ‎Dishes - ‎Beverages

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Indonesia is a vast, sprawling island nation in SE Asia with well over13,000 islands. Of Indonesia's dozen or so major islands, Bali, Sumatra and Java are .










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Gado Gado is a tossed salad mix that usually consists of cut cabbage, watercress, bean sprouts, sliced up cucumbers, fried tofu, cut and also steamed ...


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Balinese Chicken (Ayam Bumbu Bali) | Indonesian Food Recipes ...
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Balinese Chicken (Ayam Bumbu Bali): Bali Style, Asian Food, Balinese Chicken




Top 10 Best Bali Food

  • Thousands of islands with different cultures make up Indonesia, so no wonder its food is just as diverse. To complement the holiday experience on Bali, you would not want to miss out on its assortment of dishes.
    These include interesting and exotic selections such as 'lawar', 'bebek betutu', the Balinese satay version known as 'sate lilit', and the island’s famed 'babi guling' whole spit-roast pig. The Balinese have a rich collection of snacks, cakes and desserts for your sweet tooth too!
  • 1
    Sate Varieties
    Sate Varieties
    Sate (or “satay”) are marinated, skewered and grilled meats, served with spicy sauce, and may consist of diced or sliced chicken, goat, mutton, beef, pork, fish, tofu, eggs or minced blends. Bali’s own variant is sate lilit, made from minced beef, chicken, fish, pork, or even turtle meat, which is then mixed with coconut, coconut milk, and a rich blend of vegetables and spices. Wrapped rather than skewered around bamboo, sugar cane or lemongrass sticks then grilled, sate lilit can be enjoyed with or without sauce.
    2
    Nasi Ayam and Nasi Campur
    Nasi Ayam and Nasi Campur
    Bali’s own take on ‘chicken rice’, nasi ayam and nasi campur can be found served at many warungs (small eateries) and restaurants throughout the island. The dish is mainly white rice served with many different elements of Balinese delights, from a bit of babi buling or betutu as the main meats, together with mixed vegetables and a dab of the iconic spicy hot sambal matah – sometimes served with a bowl of soup. For those who do not want it too spicy, simply ask for it without the sambal.
    3
    Bebek and Ayam Betutu
    Bebek and Ayam Betutu
    Betutu is an iconic Balinese favourite, consisting of a whole chicken or duck stuffed with traditional spices, wrapped in banana leaves, then enveloped tight in banana trunk bark before it’s baked or buried in a coal fire for 6 to 7 hours. The result is a rich and juicy, succulent feast with all meat easily separated from bones. Betutu is the Balinese slow-cooked luscious equivalent of babi guling for ‘non-pork eaters’.
    4
    Babi Guling
    Babi Guling
    Babi guling is an all-time favourite, consisting of spit-roast pig stuffed with rich traditional spices and vegetable mixes such as cassava leaves, slowly ‘rolled’ over (hence its name, guling means ‘to roll’) a coal fire. The crisp brown skins are prized, while the meat is a tender and juicy treat. At first the dish was a communal treat only during special festivities and ceremonies, but now babi guling can be found widely served at warungs and restaurants specialising in this dish.
    5
    Tahu and Tempe
    Tahu and Tempe
    Among the most versatile of food items, tahu (tofu) and tempe come in various preparations, some as savory snacks, and some as accompaniments and even main course dishes. These soy bean curds may be fried, stuffed and battered. Many Indonesian dishes, especially those that have the main portions of rice, include tempe crackers, while the most favourite tahu snack are the stuffed and fried versions which usually include a mixture similar to spring rolls.
    6
    Jimbaran Seafood
    Jimbaran Seafood
    The line-up of beachside cafés on Muaya beach in Jimbaran Bay typically serves grilled fresh caught seafood, ranging from shrimp, clams, crabs, calamari, lobsters and a wide assortment of fish. But in terms of taste, the secret lies in each of the café owner’s recipes of barbecue sauce and condiments – usually in the form of homemade sambal, which has collectively become known as “sambal seafood – Jimbaran style”. From sweet-sour blends to the typical hot and spicy... tasting is believing!
    7
    Pepes and Tum
    Pepes and Tum
    Pepes is an Indonesian Sundanese cooking method using banana-leaf as food wrappings. The small package is sewed with thin bamboo sticks at both ends, and either steam-cooked, boiled or grilled. It is most commonly used to prepare fish as “pepes ikan” or meat, chicken, tofu or vegetables. Tum takes on a different form, with the wrapping folded and stitched at one top end, and usually steam-cooked. The banana-leaf wrapping provides a special aromatic appeal to the cooked blend.
    8
    Lawar
    Lawar
    Lawar is a traditional mix containing fine chopped meat, vegetables, grated coconut and spices. Sometimes, and in some areas, lawar is prepared using fresh blood mixed with the meat and spices to strengthen the flavour. Lawar are usually served immediately after preparation as it cannot be kept long. There are two main types of lawar, white and red. The white version usually does not contain any meats or blood.
    9
    Traditional Cakes and Desserts
    Traditional Cakes and Desserts
    Traditional cakes are collectively referred to as jajanan pasar (traditional market cakes), originally used to accompany ceremonial offerings, but now have found their way to the markets as daily coffee time favourites. The varieties abound, but the ingredients usually include rice flour, glutinous rice, sugar, coconut and tropical fruits. Wajikpancongjaja batun bedilbubuh injingodohpisang rai, and kelepon are typical varieties.
    10
    Nasi Goreng
    Nasi Goreng
    Nasi Goreng is Indonesia's fried rice, one of the nation's most notable dishes. Nasi Goreng is pre-steamed rice stir-fried with a combination of meats and vegetables, ranging from scrambled eggs, diced beef, strips of chicken, shrimp, anchovies, lamb, crab, green peas, onions, shallots and a blend of sweet soy sauce or kecap manis and hot chili sauce. The presentation usually features the typical toppings: sliced tomatoes and/or cucumber, fried shallots, fish or shrimp krupuk crackers and mixed pickles or acar.


Examples of Balinese dishes, such as sate lilit, nasi kuninglawar, and lala manis sambal condiment



Balinese preparing pork satay for communal religious ceremony




Balinese Babi guling or roasted suckling pig




Bebek betutu (smoked duck)




Balinese nasi campur with meat and fish versions of sate lilit

Soto babi, Balinese pork soto


Telur bumbu from Bali (boiled eggs in a hot and spicy sauce)
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