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CYCLOPENTANONE lit. survey



Patent survey ODS format

Properties

Chemical formula      C5H8O
Molar mass     84.12 g/mol
Appearance     clear, colorless liquid
Odor         peppermint-like
Density     0.95 g/cm3, liquid
Melting point     −58.2 °C
Boiling point     130.6 °C /760 Torr
Solubility in water    Slightly soluble
cycllopentanone

Cyclopentanone is a kind of important fine-chemical intermediate, it is the raw material of spices and medicine industry, can be used for preparing novel fragrance methyl dihydrojasmonate, white orchid ketone, 2 n hexyl cyclopentanone and multiple anti-inflammatory, cancer therapy drug, also can synthetic rubber, also for the synthesis of Biochemical Research, sterilant and weedicide.

The primary synthetic methods of current cyclopentanone is by pyrolysis of  hexanodioic acid(adipic acid also mainly produced  for NYLON6-6)   and cyclopentene oxidizing, but its raw material hexanodioic acid and cyclopentenes derive from fossil energy, and severe reaction conditions.

It is produced by several chemical manufacturers globally.

Some Key Producers of Cyclopentanone:

  1. BASF SE (E.C.)

  2. Rhone Poulenc/RhodiaSA/Syensqo  (E.C.)

  3. Zeon Corporation (Japan)

  4. Sinopec (China Petroleum & Chemical Corporation) (China)

  5. Zhejiang NHU Co., Ltd. (China)

  6. Alkali Metals Ltd.  (India)

Patent activity of some Key producers


BASF
BASF patents
CY-1115779-T1 METHOD FOR PREPARING CYCLOPENTANONE 2004-09-23
CY-1115779-T2 Process for the preparation of cyclopentanone 2007-06-04
JP-2013502398-A 4-pentenoic acid production method 2009-08-21
US-6344580-B1 Process for the preparation of 2,2-dimethyl-5-(4-chlorobenzyl) cyclopentanone and an intermediate useful therefore 2000-06-12
EP-1601638-A1 Method for producing and purifying cyclopentanone 2003-02-26
DE-3916140-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
DE-3916139-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
DE-3916138-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
EP-0266687-A2 Process for the manufacture of cyclopentanone 1986-11-07
DE-3878356-D1 METHOD FOR PRODUCING CYCLOPENTANONE. 1987-09-09
US-6316659-B1 Method for producing cyclopentanone and cyclopentene-1-carboxylic acid and their esters 1997-09-09
EP-1084096-A1 Method for producing cyclopentanone 1998-05-28
DE-10308489-A1 Process for the preparation of cyclopentanone and caprolactone from dicarboxylic acid solution 2003-02-26
DE-10319489-A1 Process for the preparation of cyclopentanone 2003-04-30
JP-S61218548-A Manufacture of 2-alkyl-cyclopentanone 1985-03-09
JP-H037242-A Production of cyclopentanone 1989-05-18
US-2007244272-A1 Method for Separating Ammonia and Water From Mixtures, Arising During The Production of Polyamides 2004-06-02
GB-999851-A Process for the conversion of cyclic ketoximes 1961-06-10
GB-1112397-A Processing mixtures containing acetic acid 1964-09-11
GB-728522-A Improvements in the production of pure adiponitrile 1951-10-13
US-2007167318-A1 Catalytically active composition and the use thereof in dehydration methods 2004-01-30
US-3301891-A Production of cycloaliphatic nitrates 1956-02-24
GB-830630-A Improvements in the production of lactams from oxime hydrochlorides 1956-06-02
GB-714220-A Process for exploiting the by-products from the manufacture of nitrogenous compounds having an open or cyclic chain of six saturated carbon atoms 1951-08-04
GB-788436-A Improvements in the production of cycloaliphatic ketoximes and their hydrochlorides 1955-08-05
GB-1396985-A Process for the production of aliphatic or cycloaliphatic secondary or tertiary amines 1971-04-15
GB-1390465-A Production of alpha,beta-unsaturated ketones 1971-10-13
GB-738888-A Improvements in the production of oximes 1952-06-21
GB-1048074-A Production of lactams by rearrangement of cyclic ketoximes 1962-07-25
GB-888501-A Production of bicyclo-[2,2,1]-heptadiene-(2,5) 1959-08-13
DE-3878356-D1 METHOD FOR PRODUCING CYCLOPENTANONE. 1987-09-09
DE-3916139-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
DE-3916138-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
DE-3916140-A1 Substd. cyclopentanone or formyl-cyclopentanone derivs. prodn. 1989-05-18
DE-3771657-D1 METHOD FOR PRODUCING CYCLOPENTANONE. 1986-11-07



 Zeon Corporation
Zeon patents
JP-2012219060-A Method of producing cyclopentanone 2011-04-08
JP-2017178824-A Method for producing cyclopentanone 2016-03-29
JP-2007191445-A Apparatus and method continuously producing cyclic ketone compound 2006-01-20
EP-0016650-A2 2-Cyclopentyl-cyclopentanone, fragrance or flavouring compositions containing it and their use 1979-03-26
JP-S597129-A Preparation of cyclopentanone 1982-07-05
JP-S58203932-A Production of cyclopentanone 1982-05-21
JP-S58150534-A Preparation of cyclopentanone 1982-03-03
JP-2004131439-A Method for producing 2,5-disubstituted cyclopentanone compound and 2,5-disubstituted cyclopentanol compound 2002-10-11
JP-2008088071-A Method for producing 2-cyclopentyl cyclopentanone compound 2006-09-29
JP-H02306929-A Production of 2,3-disubstituted cyclopentanone mixture 1989-05-23
JP-2001335527-A Method for producing cyclopentanone 2000-05-30
JP-H1072399-A Production of 2-substituted cyclopentanone 1996-08-30
JP-2003040821-A 2,5-disubstituted cyclopentanone and perfume composition 2001-07-30
JP-2020169202-A Method for producing cyclopentanone 2020-07-06
EP-0612715-A2 Fragrant composition 1989-05-23
US-5372994-A Fragrant composition 1989-05-23
JP-S604179-A Production of delta-lactone 1983-06-20
JP-S604180-A Production of delta-substituted-delta-lactone 1983-06-20
JP-S57197275-A Production of alpha-lactone 1981-05-29
JP-S57209285-A Preparation of delta-lactone 1981-06-17
JP-S57209284-A Preparation of delta-lactone 1981-06-17
JP-S58170777-A Preparation of 8-lactone 1982-03-31
JP-2004083446-A Equilibrium mixture, its manufacturing method and method for manufacturing 1-alkoxy-2-oxabicyclooctane compound 2002-08-23
JP-2000119691-A Detergent and cleaning method using the same 1998-10-12
JP-H01171496-A Production of 9alpha-hydroxysteroid 1987-12-25
JP-2000119693-A Detergent and cleaning method using the same 1998-10-12
JP-H06179635-A Production of steroid intermediate 1993-07-19
JP-H08262711-A Positive type resist composition 1995-03-24
JP-S5756401-A Wood preservative 1980-09-19
JP-S5748931-A Preparation of carbonyl compound 1980-09-09
JP-S5748934-A Preparation of 2-substituted cycloalkanone 1980-09-10
JP-S5980619-A Oxidation of cyclopentene 1982-10-29
JP-2002121394-A Curable composition 2000-10-13
JP-H10123725-A Developer for photosensitive polyimide 1996-10-18
JP-2001261609-A High-purity cyclopentane derivative having oxygen- containing group, method for producing the same and perfumery composition containing the same 2000-03-22
JP-2019133104-A Positive resist composition, method for forming resist film, and method for manufacturing laminate 2018-02-02
JP-S55120533-A Preparation of 2-alkyl-2-cyclopentenone 1979-03-09
JP-S61122244-A Production of cycloalkanecarboxylic acid compound 1984-11-19
JP-2008228804-A Deodorant and fiber product using the deodorant 2007-03-16
JP-2004137177-A Method for producing 2-oxocyclopentane carboxylate 2002-10-16
JP-2004083447-A 2-oxabicyclo[3.3.0]octane compound, its manufacturing method and optical resolution agent 2002-08-23
WO-0022081-A1 Heptafluorocyclopentane composition, method of cleansing, and method of recovery 1998-10-09
JP-H05271142-A Production of carbonyl compound 1992-03-27


Rhone Poulenc/RhodiaSA/Syensqo

US-5600013-A Preparation of cyclic ketones Rhone-Poulenc Chimie 1993-05-28
US-5856581-A Preparation of cyclic ketones Rhone-Poulenc Chimie 1993-05-28
DE-69403882-D1 Process for the C-alkylation of a ketonic compound Rhone Poulenc Chimie 1993-11-22
EP-0626364-A1 Process for the preparation of a cyclic ketone Rhone-Poulenc Chimie 1993-05-28
EP-0722432-A1 Method for preparing of mono or di-2-substituted cyclopentanone Rhone-Poulenc Agrochimie 1993-10-07


Sumitomo

JP-S57128649-A Cyclopentanone derivative 1981-01-30
JP-S60224656-A Production of cyclopentanone derivative 1984-04-20
JP-S6092234-A Production of cyclopentanone 1983-10-26
JP-S57188540-A Preparation of cyclopentanone compound 1981-05-13
JP-H07118693-A Cleaning solution for sensitizing agent production device, cleaning method using the same, cleaning solution for resist solution preparation device and cleaning method using the same solution 1993-08-30
JP-H04149153-A Cyclopentanealdehydes and production thereof 1990-10-12
JP-2004168774-A Method for producing 2-bromocyclopentanone 2002-11-08
JP-S6064943-A Production of optically active 4-hydroxycyclopentenone 1983-08-10
JP-S59187788-A Method for separating cyclopentenone 1983-04-08
JP-2004109423-A Color photosensitive resin composition 2002-09-18
JP-S6137756-A Production of cyclopentylacetic acid 1984-07-30
JP-H06320128-A Washing solution and method for spin coater line piping 1993-05-18
JP-S61106537-A Production of cyclopentylacetic acid ester 1984-10-30
JP-H0665133-A Production of optically active 4-hydroxy-2-cyclopentenone 1992-08-20
JP-S62223149-A Production of optically active 4-hydroxycyclopentenone 1986-03-25
JP-H08143542-A Unsaturated aldehyde derivative, intermediate, their production and use 1994-11-24


Last worldwide patents for 2020 to 2024 Period 

 Total 195 patents mostly from China corporation and /or Universities (90% from Chnia , 10% rest of world)



All details   : patents2020_2024


CYCLOPENTANONE SYNTHESIS

Cyclopentanone from adipic acid




Adipic acid is widely available from various source , being  one of the raw material used to produce NYLON 6-6 by reaction with  hexamethylene diamine .The production of cyclopentanone is generally done in continuous with a proprietary catalyst at temperature in the 250/300° c range depending on the catalyst used  .

The  cyclopentanone  chemical yield  is over 95% , the purification is done by distillation
cyclopentanone



Cyclopentanone from cyclopentene

Cyclopentene (liquid boiling point 45°c/760 torr)  is produced industrially in large amounts by steam cracking of naphtha.

By oxydation it can lead to cyclopentanone  using various catalyst  and solvants .

Here some examples  of patents taken by different chemical corporations around the world


Oxydation with hydrogene peroxide
 (Shandong Chambroad Petrochemicals Co procedure 2024 )

The process consist of  oxidizing cyclopentene with hydrogen peroxide aqueous solution, in presence of  a specific catalyst, generating cyclopentanol by  water addition on cyclopentene  under the action of an acid center,

The cyclpentanol generated  is oxydized into  cyclopentanone  under the action of hydrogen peroxide and a titanium silicon molecular sieve,

This is a  one-step method  thanks  to  the action of a modified molecular sieve; the production method has the advantages of simple operation, mild condition, high selectivity of cyclopentanone (.CN118666655A  Worldwide applications  2024 CN Shandong Chambroad Petrochemicals Co Ltd  claiming 50% conversion of cyclopentene into cyclopentanone with 99% selectivity )


lab_experimental procedure 

cyclopentanone



Oxydation with hydrogene peroxide   Nippon Zeon recipe 1982

JP-S5980619-A    Oxidation of cyclopentene     Nippon Zeon Co Ltd  1982-10-29                                                                                                                                               
Abstract
To obtain an oxygen-containing compound useful as a raw material of perfumes, pharmaceuticals, agricultural chemicals, etc., continuously, in high yield, by oxidizing cyclopentene in the presence of a palladium compound and a molybdenum-based heteropolyacid compound in combination with hydrogen peroxide. CONSTITUTION:An oxygen-containing compound such as 2-cyclopenten-1-one, cyclopentanone, cyclopentanol, etc. is prepared economically, in an industrial scale, without loss of the catalytic activity, by oxidizing cyclopentene in the presence of (A) a palladium compound, (B) a molybdenum-based heteropolyacid compound and (C) hydrogen peroxide, at 20-80 deg.C, preferably using a solvent which dissolves at least a part of the components A-C. The molar ratios of A and B to cyclopentene are preferably about 0.1-0.005 and 2-20, respectively, and that of C to palladium is about 2-20, from the economical view point.

cyclopentanone

Oxydation with nitrous oxide  (N2O)  BASF procedure 2007

WO-2008148661-A1    Method for producing cyclopentanone     Basf Se  2007-06-04
Abstract
The invention relates to a method for producing cyclopentanone. Said method comprises the step of reacting a mixture (G1), which contains at least cyclopentene, with a mixture (G2), which contains at least dinitrogen monoxide. The reaction is carried out in at least one reactor (R1) having channels with a diameter in the range of 0.1 mm to 50 mm, the reactor comprising at least two zones (Z1) and (Z2) having channels with different diameters and the diameters of the channels of zone (Z1) being smaller than the diameter of the channels of zone (Z2).

According to a preferred embodiment, the reaction is carried out in the temperature range between 270 and 300 0 C and at a pressure of 260 to 350 bar, in particular 280 bar.
The reaction conditions are preferably selected such that the N 2 O conversion is more than 80% and the cyclopentene conversion is more than 50%.


Pilot examples in details
cyclopentanone



Oxydation with  oxygene ( Sumitomo recipe )

JPS6092234A Current Assignee    Sumitomo Chemical Co Ltd  1983

Example 1 Cyclopentene of 84, 19 and ethanol of 85.39 were charged into a 200 cc round bottom flask with a cooler, 19.4g bismuth nitrate and 10.6P as catalyst
After adding a commercially available 5% PD-activated carbon supported catalyst (manufactured by Nippon Engelhard Co., Ltd.), 99% pure oxygen (the remainder being nitrogen) was continuously supplied at 51/r into the well-stirred liquid. The reaction temperature was set at 45°C, and after 4 hours of reaction, the reaction product was analyzed, and the conversion  of cyclopentene was 75%. The selectivity for cyclopentanone was 72%.

Comparative Example 1 The same treatment as in Example 1 was carried out except that bismuth nitrate was not added. As a result of analysis of the obtained reaction product, the conversion rate of cyclopentene was 26%, and the selectivity of cyclopentanone was 1% or less.

lab_procedure_example (Sumitomo1983)

cyclopentanone


Isomerization of cyclopentene oxide

JP-S6330446-A     Idemitsu Petrochem Co Ltd, 1986-07-23

Abstract
PURPOSE:To obtain the titled compound, which is a raw material for sebacic acid, intermediate raw material for medicines, etc., by bringing cyclopentene oxide into contact with a catalyst carrying palladium in the presence of hydrogen with a long catalyst life without causing corrosion of a reactor. CONSTITUTION:Cyclopentene oxide is isomerized in the presence of a catalyst carrying palladium and hydrogen a 10-100 deg.C, preferably 20-70 deg.C temperature under 0.01-11kg/cm<2>, preferably 1-6kg/cm<2> (absolute pressure) of hydrogen partial pressure to afford the aimed cyclopentanone. The amount of the catalyst used is within the range of 0.001-0.1g atoms, preferably 0.001-0.05g atoms expressed in terms of palladium atoms based on 1mol cyclopentene oxide.

cyclpentanone


More Patents references using cyclopentene as raw material



Cyclopentanone From cyclopentanol

Cyclopentanol can be producded starting from cyclopentene (more info here)  and also very often depending on demand from cyclopentanone !  .

CN102603506A current Assignee  Paierke chemical materials (Qidong) Co., Ltd.  2012




The invention relates to a method for preparing cyclopentanone through cyclopentanol dehydrogenation. The method comprises the steps of carrying out catalytic dehydrogenation and rectification reactions on the raw material cyclopentanol so as to directly obtain the high-purity cyclopentanone, wherein the catalytic dehydrogenation temperature is 85-115 DEG C, the system pressure is 100-300mmHg, and granular Raney nickel type metal alloy comprising 53% of Al, 44% of Ni and 3% of Mo is adopted as a catalyst in the dehydrogenation reaction; and the cyclopentanol load WWH of the catalyst is 2-4hr-1. The gas-phase dehydrogenation reaction product directly enters in a rectifying column of which the number of theoretical plates is 45 to be purified and the reflux ratio of the rectifying column is controlled to be (2:1)-(5:1)to ensure that a cyclopentanone product with the purity of more than 99.9% is obtained. Compared with the prior art, the method disclosed by the invention has the advantages that the energy consumption is low; the use efficiency of the catalyst is high; the production cost is greatly reduced; the purity of the obtained cyclopentanone product is more than 99.9%; and a green and environment-friendly production process is provided.
cyclopentanone

More patents using cyclopentanol as raw material



Cyclopentanone From furfural


    Furfural is a biomass-derived material, and is industrially produced on a large scale from inexpensive agricultural and forestry wastes (such as corn cobs, bagasse, cottonseed hulls, and the like) as a raw material. The furfural and the cyclopentanone both have five carbon atoms, so that the furfural is directly converted into the cyclopentanone, and the application value is important. The preparation of cyclopentanone by hydrogenation rearrangement is also gradually a hot spot of biomass research especially in China

Furfural is an organic compound derived from agricultural byproducts such as corncobs, oat, wheat bran, and sawdust. It is produced through the acid hydrolysis of pentosans, which are polysaccharides that yield pentoses (five-carbon sugars) like xylose upon hydrolysis.  The raw materials are first cleaned and ground to increase the surface area for hydrolysis.The ground material is treated with a dilute acid (usually sulfuric acid) at elevated temperatures (around 150-200°C). This step hydrolyzes the pentosans into pentose sugars, primarily xylose.The pentose sugars undergo dehydration in the presence of the acid catalyst, leading to the formation of furfural. The furfural is then separated from the reaction mixture through steam distillation. The furfural vapor is condensed , collected and purified by distillation .

cyclpentanone

Firstly  furfural is  hydrogenated to generate furfuryl alcohol, the furfuryl alcohol is rearranged to generate 4-hydroxy-cyclopent-2-enone  (PIANCATELLI rearrangement ),
 
The 4-hydroxy-cyclopent-2-enone is then  subjected to hydroxy dehydration and double bond hydrogenation to generate cyclopentanone,


cyclpentanonecyclopentanone




 The temperature required by PIANCATELLI rearrangement reaction of furfuryl alcohol is high, but the higher temperature can cause side reactions such as hydrogenation of carbon-carbon bonds in the furfural to generate tetrahydrofurfuryl alcohol, methyl furan and even cyclopentanol . Therefore, the process for preparing cyclopentanone by using furfural it is difficult to  achieve both the hydrogenation step and PIANCATELLI rearrangement of furfuryl alcohol. In order to reduce the generation of cyclopentanol and other byproducts, the whole reaction temperature must be reduced, but the PIANCATELLI rearrangement reaction rate of furfuryl alcohol is very slow, and in order to improve the rearrangement reaction rate of furfuryl alcohol PIANCATELLI, a large amount of water is required to be added into the reaction system, which causes the concentration of substrate furfural to be too low, thereby resulting in low production efficiency and high subsequent separation cost.

On top of this  the intermediate furfuryl alcohol and 4-hydroxy-cyclopent-2-enone are easy to undergo side reactions of polymerization at the reaction temperature, and the polymeric byproduct  is sticky t

Achieving high selectivity for cyclopentanone without forming byproducts (e.g., levulinic acid, resins, or polymers) is  challenging  ,   Catalyst Stability is also an issue :  catalysts may deactivate over time due to fouling or poisoning It should be able to drive both hydrogeanation and PIANCATELLI reaction.

One pot synthesis looks possible , however  it looks more promizing to split the various  reactions  as indicated in Patent  CN-115894196-B  For the time being productivity and overall yield are modest  but a lot a research  is underway to improve this situation  as it can be seen by the various patents taken recently from China universities , China being , the first world producer for  furfural .

                                                                                                                                                                                           

Example of lab Procedures

One of latest relevant patent  :CN-115894196-B    Method for continuously synthesizing cyclopentanone  from furfural     2022-11-17    Application filed by Ningxia Xinhua Chemical Co ltd, ZHEJIANG XINHUA CHEMICAL CO Ltd, Zhejiang University ZJU   

here many more patents





Some examples of cyclopentanone use

Cyclopentanone is a versatile compound in organic synthesis, and it's used as a raw material in several important processes. Here are a few examples of where cyclopentanone plays a role:

    Synthesis of Pharmaceuticals:
        Steroid Synthesis: Cyclopentanone is often used as a starting material in the synthesis of steroid compounds, which are used in a wide range of pharmaceutical applications. For example, it can be part of the synthesis of corticosteroids or sex hormones.

  

    Synthesis of Flavor and Fragrance :
        It is used in the fragrance industry for the synthesis of certain flavor and fragrance compounds. One example is the production of methyldihydrojasmonate, which is used as a scent in perfumes. (more info on dihydrojasmonate)

Due to its chemical reactivity it can lead to different products  used in various sectors as it can be seen looking at the patent litterature



AVIATION FUEL FROM GREEN CHEMISTRY
CN-106867565-A A KIND OF PREPARATION METHOD OF HIGH DENSITY LIQUID HYDROCARBON FUEL  中国科学院大连化学物理研究所 2015-12-12 2017-06-20
 Application filed by Dalian Institute of Chemical Physics of CAS
cyclopenanone hydrocarbon fuel


In this patent, we use cyclopentanone as raw material, by a fixation equipped with dual catalyst bed Bed reactor is directly synthesized the high density aviation fuel that main component is bicyclic pentane and three pentamethylene.At first Catalytic bed, cyclopentanone under the catalysis of acid/base catalyst or metal-doped solid base, by itself aldol Condensation reaction (and hydrogenation reaction), obtains the oxygen-containing organic compound that carbon number is 15 and 10;Connect in fixed bed Second beds of continuous formula reactor, carbon number be 15 and 10 oxygen-containing organic compound in carried metal Under the catalysis of A/X type bifunctional catalysts, lower temperature (100-300 DEG C), it is solvent-free under the conditions of enter The step hydrogenation deoxidation of row one, obtains the polycyclic HC fuel of carbon number 15 and 10.Whole process avoid catalyst with The separation of product, realizes chemical industrial integrated, is conducive to the continuous prodution of Future high-density aviation fuel.

JP-H08105827-A    Solvent for pathological examination     YWako Pure Chem Ind Ltd,   1994-08-09                                                                                                                       PURPOSE: To obtain a solvent having volatility equal to that of an organic solvent such as xylene and safety equal to that of a limonene-base solvent                                                                                                                                                                                                                                                                                         
JP-H0577903-A    Garbage bag     Azetsukusu:Kk, 株式会社アゼツクス    1991-09-24          
                                                                                                                           Abstract
PURPOSE:To provide a garbage bag to which dogs or cats do not come near even when it is left alone. CONSTITUTION:A garbage bag is formed out of a synthetic resin sheet having the weight ratio of 1ppm or more of at least one of menthone, menthol, limonene, alpha-pinene, 3-methylcyclopentanone or cyclopentanone as odor components. Dogs or cats dislike the odor of these components, so that they do not come near to the bag.
                                                                                                                                                                                                                                                                               
JP-H05218092-A    Manufacture of field-effect transistor     Nec Corp, 日本電気株式会社    1992-01-28                                                                                                           
Abstract
PURPOSE:To enhance the breakdown strength, and at the same time, to reduce the capacitance between gate and source by making it difficult to allow the field concentration on the gate electrode. CONSTITUTION:An insulating film 4 and a metallic film 5 are formed on a GaAs substrate in that order. After the metallic film 5 and the insulating film 4 are anisotropically etched with a resist 6 as a mask, an operating layer 3 is etched to form a recess. Then, a resist 7 made of cyclopentanone and 2-(2- methoxy ethoxy) ethanol as the main components is coated in order to deposit a gate metal 8 while leaving resists 7a and 7b in the recess immediately below the insulating film 4 by the irradiation of ultraviolet rays and development.
                                                                                                                                                                                                                                                                                 JP-S5756401-A    Wood preservative     Nippon Zeon Co Ltd    1980-09-19                                                                                                                                                         
Abstract
PURPOSE: An oil-soluble safe wood preservative, containing cyclopentylidenecyclopentanone and cyclopentylcyclopentanone as active constituents, and having improved permeability and operational rate without irritant action and "kabure" on the skin.
CONSTITUTION: A wood preservative containing cyclopentylidenecyclopentanone and cyclopentylcyclopentanone as active constituents. The cyclopentylidenecyclopentanone is generally synthesized by condensing two molecules of cyclopentanone through dehydration, and the cyclopentylcyclopentanone is synthesized by hydrogenating the cyclopentylidenecyclopentanone. Both of them are colorless and transparent liquid substances and have a low viscosity and antimicrobial activity against fungi, e.g. wood destroying fungi or molds, which are microorganisms causing the deterioration of wood. The preservative permeates into the central part of the wood readily to keep the antiseptic (preserving) effect for a long time.    

      CN-114878557-A    Kit for rapidly detecting TNT     北京理工大学    2022-04-29                                                                                                                                                                                                                                                                                                                                                                                              Kit for rapidly detecting TNT
Abstract
The invention relates to a rapid chemical detection method for common explosive TNT, belonging to the technical field of energetic materials. First by configuring one of the components a of the different detection reagents: KOH-ethanol, benzaldehyde, diphenylamine-concentrated sulfuric acid and cyclopentanone-tetraethyl ammonium hydroxide. The preparation method of the KOH-ethanol solution comprises the following steps: weighing KOH and ethanol according to the mass ratio of 1:20, and uniformly mixing. The preparation method of the diphenylamine-concentrated sulfuric acid comprises the following steps: diphenylamine and concentrated sulfuric acid are respectively weighed according to the mass ratio of 1:200 and then uniformly mixed. The preparation method of cyclopentanone-tetraethylammonium hydroxide comprises the following steps: respectively weighing cyclopentanone, 25% tetraethylammonium hydroxide aqueous solution and ethanol according to the mass ratio of 1:2:12, adding into a beaker, and uniformly mixing. After the preparation is finished, the component A, the ammonium dodecyl sulfonate and a sample to be detected are uniformly mixed, and the TNT can be rapidly detected. The method can quickly detect the existence of TNT, is simple and convenient to operate and is suitable for application of explosion field personnel.
                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                    
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