622-96-8|1-Ethyl-4-methylbenzene| Ambeed

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Photo(bio)catalytic transformations employing light-dependent Protochlorophyllide Oxidoreductases and an unspecific Peroxygenase / submitted by Luca Léo Schmermund

Luca Léo Schmermund ;

Abstract: The limited resources on Earth as well as the energy demand of the ever-increasing population urges us to develop new sustainable processes that cover the use of renewable energy and raw materials. In this context, coupling light with biological systems or enzymes for chemical synthesis is one possible way to achieve sustainable processes as light is a powerful and almost ideal source of energy. In recent years, the field of photobiocatalysis has emerged which brought together two sustainable as well as two research-intensive fields: Photocatalysis and biocatalysis. In this thesis, photo(bio)catalytic transformations were investigated employing light-dependent protochlorophyllide oxidoreductases and an unspecific peroxygenase. In the first part of this study, the library of light-dependent protochlorophyllide oxidoreductases (LPORs) was expanded and the potential of LPORs as biocatalysts was explored. LPORs require light for their natural reaction and catalyze the NADPH-dependent reduction of a C=C in an N-heterocycle of protochlorophyllide, a precursor of chlorophyll. Five LPORs were identified by a sequence search and four of them were well expressible in Escherichia coli and displayed activity. Overall, the study showed that LPORs are easily accessible and possess properties that are required for an efficient biocatalyst. In the second part of this thesis, a light-driven in situ generation of hydrogen peroxide by different carbon nitrides (CNs) was linked to stereoselective hydroxylations catalyzed by an unspecific peroxygenase variant from Agrocybe aegerita (AaeUPO). The chromoselective behavior of the CN allowed to create photo-chemo-enzymatic cascades to form either the (S)- or the (R)-enantiomer of 1-phenylethanol starting from ethylbenzene. The combination of chromoselective photocatalysis with biocatalytic transformation was shown for the first time. The novel concept represents a new tool for controlling reactivity and stereoselectivity in organic synthesis leading to excellent stereoselectivities.

Purchased from AmBeed: 1973-22-4 ; 117358-52-8 ; 611-14-3 ; 622-96-8

Product Details of [ 622-96-8 ]

CAS No. :	622-96-8
Formula :	C₉H₁₂
M.W :	120.19
SMILES Code :	CC1=CC=C(CC)C=C1
MDL No. :	MFCD00009263
InChI Key :	JRLPEMVDPFPYPJ-UHFFFAOYSA-N
Pubchem ID :	12160

Safety of [ 622-96-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H226-H303-H304
Precautionary Statements:	P210-P240-P233-P241-P242-P270-P243-P280-P301+P312-P303+P361+P353-P301+P310-P370+P378-P331-P403+P235-P501
Class:	3
UN#:	3295
Packing Group:	Ⅲ

Application In Synthesis of [ 622-96-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 622-96-8 ]

[ 622-96-8 ] Synthesis Path-Downstream 1~35

1
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References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 3099 - 3107.

2
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

3
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[ 100-41-4 ]
[ 620-14-4 ]
[ 611-14-3 ]
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References: [1]Journal of general chemistry of the USSR,1987,p. 1042 - 1049.
Zhurnal Obshchei Khimii,1987,vol. 57,p. 1165 - 1172.

4
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[ 611-14-3 ]
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References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 437 - 444.

5
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References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 2560 - 2565.
[2]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 437 - 444.

6
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References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 437 - 444.

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References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 5284 - 5290.

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References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 5284 - 5290.
[2]Journal of the American Chemical Society,1988,vol. 110,p. 2560 - 2565.

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References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 5284 - 5290.
[2]Petroleum Chemistry,1995,vol. 35,p. 527 - 534.
Neftekhimiya,1995,vol. 35,p. 545 - 552.

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References: [1]Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases,1983,vol. 79,p. 311 - 326.

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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

13
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Yield	Reaction Conditions	Operation in experiment
	With phosphorus-silicon modified catalyst; at 360℃; under 3750.38 Torr; for 4h;	The catalyst sample was charged into a fixed bed reactor,The loading was 6.5g. The reaction was carried out using toluene (> 99%) and polymerization grade ethyl as raw materials,Ethylene flow rate of 13.4 g / h,The toluene flow rate was 176. Og / h.The molar ratio of toluene to ethylene was 4.0,The total material airspeed is 29.2 hours 4,The reaction temperature is 360 C,The pressure is 0.5MPa.The results of the reaction conversion and the selectivity of the various products are shown in Table 1,Among them, the selectivity of the three ethyltoluene products has a wide distribution range,Can meet the different requirements of different business users and selectivity.

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 437 - 444.
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 7694 - 7696.
[3]RSC Advances,2014,vol. 4,p. 28786 - 28793.
[4]ChemCatChem,2016,vol. 8,p. 1945 - 1950.
[5]Patent: CN104230632,2016,B .Location in patent: Paragraph 0024; 0025.

14
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

15
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

16
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.
[2]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

17
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

18
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References: [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 1832 - 1839.

19
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References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 5284 - 5290.
[2]Journal of the American Chemical Society,1988,vol. 110,p. 2560 - 2565.

20
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References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 5284 - 5290.
[2]Journal of the American Chemical Society,1988,vol. 110,p. 2560 - 2565.

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References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2887 - 2893.

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References: [1]Collection of Czechoslovak Chemical Communications,1995,vol. 60,p. 412 - 420.

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References: [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1957,vol. 60,p. 69.
Chem.Abstr.,1959,p. 6116.

24
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References: [1]Journal of Catalysis,2004,vol. 223,p. 54 - 63.

25
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[ 6833-47-2 ]

References: [1]Russian Journal of Organic Chemistry,1998,vol. 34,p. 86 - 89.

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In toluene; at 150℃; under 3620.13 Torr;Gas phase;Conversion of starting material;	The column containing the dried adsorbent was placed in a heated enclosure at 150 C. and maintained at a pressure of 70 psig using back pressure regulators. Liquid phase toluene desorbent was directed into the columns at measured rates. A liquid phase 2 mL pulse of a feed containing equal parts normal nonane, ethylbenzene, para-xylene, meta-xylene, ortho-xylene, para-methylethylbenzene, meta-methylethylbenzene, ortho-methylethylbenzene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene and 1,3,5-trimethylbenzene was introduced and the desorbent flow was resumed. While in the column, the C8 alkylaromatic hydrocarbons and C9 alkylaromatic hydrocarbons were maintained in the liquid phase. The effluent of the system was analyzed by gas chromatography to obtain the composition of the effluent. FIG. 3shows the concentration profiles of the effluent beginning with the background level of toluene desorbent. The concentrations of each individual species in a class were summed and the sum of the concentrations plotted. A region of effluent enriched in C8 alkylaromatic hydrocarbons elutes prior to a region enriched in C9 alkylaromatic hydrocarbons demonstrating that separation of the C8 alkylaromatic hydrocarbons from the C9 alkylaromatic hydrocarbons is occurring.

Yield	Reaction Conditions	Operation in experiment
5.3%		EXAMPLE 26B Toluene and ethylene were reacted over the Ba-Modified ZSM-11 at 400 C. The feed WHSV for toluene was 7.0 and for ethylene was 0.5. Conversion of toluene was 5.3% and the yield of para-ethyltoluene in the ethyltoluene produced was 89.0%.

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[ 103-65-1 ]
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References: [1]Kinetics and Catalysis,2010,vol. 51,p. 56 - 62.
[2]Kinetics and Catalysis,2010,vol. 51,p. 56 - 62.

29
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References: [1]Kinetics and Catalysis,2010,vol. 51,p. 56 - 62.

30
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References: [1]Kinetics and Catalysis,2010,vol. 51,p. 56 - 62.

31
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[ 622-96-8 ]
[ 1595-05-7 ]
[ 1595-11-5 ]
[ 1595-01-3 ]
[ 1595-10-4 ]

References: [1]European Journal of Inorganic Chemistry,2009,p. 3016 - 3024.

32
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[ 1758-85-6 ]
[ 13632-95-6 ]

References: [1]European Journal of Inorganic Chemistry,2009,p. 3016 - 3024.

33
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[ 620-14-4 ]
[ 611-14-3 ]
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[ 108-88-3 ]

References: [1]Applied Catalysis A: General,2012,vol. 417-418,p. 76 - 86.

34
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[ 105-05-5 ]
[ 253185-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ZSM-11; at 380 - 420℃;	The embodiment at the same time providing one-step synthesizing methyl ethylbenzene and diethylbenzene method, with the embodiment 1 only in the different: the composition of the raw materials and a slightly different reaction parameters, the raw material is benzene, toluene, and ethylene, benzene and toluene ratio of 1 : 1.5, the method comprises pre-processing phase, and the post-processing stage of the reaction stage, specific steps are as follows: (1) pre-treatment phase: A) benzene, toluene after benzene, toluene heat exchanger heating to 120 C, enters the benzene, toluene gasifier, gasification and enters into the heating furnace is heated to 350 C; B) ethylene enters the ethylene gasifier and heating to 18 C; Ethylene and benzene and toluene feed ratio is 17, and toluene benzene including the follow-up of the amount of benzene, toluene and benzene in the system, the mixture of toluene and ethylbenzene enters the benzene, toluene that part of the gasifier; (2) reaction stage: The pretreatment latter benzene, toluene and ethylene-access hydrocarbon for carrying out the alkylation reaction in the reactor, in the alkylation reactor containing a plurality of catalyst bed layer, high ratio of the diameter of the catalyst bed is 0.75, the catalyst bed of catalyst is employed in the ZSM series of ZSM-11 molecular sieve catalyst, the alkylation reactor WHSV=11 vhsv the gross weight of; the inlet pressure to the alkylation reactor 0.9MPaG; is inserted to each of the laminated-tight layer of the catalyst bed the temperature measured by the temperature measurement element to the reaction starting temperature, the temperature is controlled at 400 C, bottom supporting ceramic ball in the temperature measured by the temperature measuring element of the bed as the temperature of the end of the reaction, the temperature is controlled at 420 C; the reaction temperature is controlled at 380 C; between each section of the catalyst bed is provided with a and benzene, toluene gasifier and ethylene pipeline connected with the gasifier, in this way the heat in the reaction process can be through relatively cold benzene, toluene and ethylene to digestion, and control the ethylene flow regulating bed temperature rise is kept at 20 C the left and the right, control acute leng Ben, toluene (or benzene, toluene, ethylbenzene) of adjusting the flow rate of the relative stability of the reaction temperature is maintained, to ensure the reaction temperature is maintained at a suitable temperature; after reaction for a period of time, to the reaction solution for chromatographic analysis, wherein the ethylbenzene (O, between, the two ethylbenzene, mainly to the location between the) total content exceeds 8% and interpositus diethylbenzene to para diethylbenzene content ratio of 6:1; methyl ethylbenzene (O, between, methylbenzensulfonate ethylbenzene, mainly to the location between the) total content exceeds 4%, and interpositus methyl ethylbenzene with para-methyl ethylbenzene content ratio of 3:1; can stop the reaction after processing; (3) post-treatment: 1) the alkylation reactor discharging through the heat exchanger, cooling to the 330 C, enters the benzene, toluene recovery system, the top of the tower pressure is 0.8, the overhead temperature is 190 C, the sump temperature is 280 C, after the rectification and purification, said benzene, toluene recovery system applicable for the top of the tower, the mixture of toluene and ethylbenzene, is hot tower cauldron material methyl ethylbenzene, coarse ethylbenzene and diethylbenzene; said benzene, toluene recovery system of the tower in benzene, toluene and ethylbenzene a portion of the reflux enters the benzene, toluene recovery system, in addition a part of the access-benzene, toluene gasifier, reflux ratio is 1.2; 2) the said benzene, toluene recovery system tower cauldron material access to an ethylbenzene rectification system, ethylbenzene column of the rectification system is negative pressure, the top of the tower pressure is 0.117MPaG, the bottom of the tower pressure 0.14MPaG, the overhead temperature is 160 C, the sump temperature is 218 C; reflux ratio is 2.5; after the rectification and purification, to the top of the tower the ethylbenzene rectification system ethylbenzene, the total content of the material before rectifying the total content of 5%, the main component of tower cauldron material is a ethylbenzene and diethylbenzene; 3) in the of the ethylbenzene rectification system into tower cauldron material in methyl ethylbenzene rectification system, methyl ethylbenzene column of the rectification system is negative pressure, the top of the tower pressure is 0.006MPaG, the bottom of the tower pressure is 0.019MPaG, the overhead temperature is 80 C, the sump temperature is 135 C; reflux ratio is 3.8; after the rectification and purification, ethylbenzene rectification system of the invention involves the top of the tower in methyl ethylbenzene of a certain purity, t...

References: [1]Patent: CN105622308,2016,A .Location in patent: Paragraph 0051-0065.

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[ 611-14-3 ]
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[ 1595-05-7 ]
[ 1595-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With (5-phenyl-3-(trifluoromethyl)-1H-pyrazole)2PdCl2; ethylaluminum dichloride; at 30℃; under 7500.75 Torr; for 1h;Autoclave;Catalytic behavior;	General procedure: Oligomerization and Friedel-Crafts alkylation reactions were carried out in a 40mL high-pressure reactor, which was dried at 100 C and cooled under nitrogen to the desired temperature before use. An appropriate amount of pre-catalyst was added tothe reactor under nitrogen together in degassed toluene (10 mL)and an appropriate amount of ethyl aluminium dichloride added with a syringe. Immediately after the addition of theEtAlCl2, the reactor was charged with ethylene and the reactor temperature was maintained at the desired temperature. Ethylene pressure was set at the desired pressure maintained at thispressure during the reaction After the set reaction time, excess ethylene was vented and the reaction quenched by adding 2MHCl in methanol. The oily yellow product formed was filtered to remove any solid matter, washed with 2MHCl in methanol and volatiles removed in vacuo. All experiments were run in triplicate.

References: [1]South African Journal of Chemistry,2016,vol. 69,p. 236 - 243.

Historical Records

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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[ 622-96-8 ]

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P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 622-96-8

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