CN111450857B - Catalyst and preparation process of tert-butyl isothiocyanate - Google Patents

Catalyst and preparation process of tert-butyl isothiocyanate Download PDF

Info

Publication number
CN111450857B
CN111450857B CN202010403496.2A CN202010403496A CN111450857B CN 111450857 B CN111450857 B CN 111450857B CN 202010403496 A CN202010403496 A CN 202010403496A CN 111450857 B CN111450857 B CN 111450857B
Authority
CN
China
Prior art keywords
tert
butyl isothiocyanate
hydrogen chloride
drying container
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202010403496.2A
Other languages
Chinese (zh)
Other versions
CN111450857A (en
Inventor
任天瑞
陈福勇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Zaitou Biotechnology Co ltd
Original Assignee
Jiangsu Parrini New Material Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangsu Parrini New Material Technology Co ltd filed Critical Jiangsu Parrini New Material Technology Co ltd
Priority to CN202010403496.2A priority Critical patent/CN111450857B/en
Publication of CN111450857A publication Critical patent/CN111450857A/en
Application granted granted Critical
Publication of CN111450857B publication Critical patent/CN111450857B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/16—Isothiocyanates
    • C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
    • C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a catalyst and a preparation process of tert-butyl isothiocyanate, wherein the catalyst is dry hydrogen chloride gas. Taking 70-85 parts of ammonium thiocyanate, 200 parts of water, 65-90 parts of 85% tertiary butanol and 200-250 parts of 30% hydrochloric acid according to parts by weight, dissolving ammonium thiocyanate in water, adding 85% tertiary butanol, heating, dripping 30% hydrochloric acid, standing for layering, taking an upper material, transferring the upper material into a drying container, heating to 50-60 ℃, vacuumizing, introducing dry hydrogen chloride gas into the vacuumizing drying container, recovering normal pressure to the drying container, closing a valve, maintaining for 30+/-5 min, and then performing nitrogen replacement to obtain tert-butyl isothiocyanate. According to the invention, the dried hydrogen chloride gas is used as the catalyst for preparing the tert-butyl isothiocyanate, the hydrogen chloride is easy to separate, no byproduct is generated, the preparation of the tert-butyl isothiocyanate reaches more than 98%, and meanwhile, the preparation environment of the tert-butyl isothiocyanate can be effectively improved.

Description

Catalyst and preparation process of tert-butyl isothiocyanate
Technical Field
The invention relates to a catalyst for preparing tert-butyl isothiocyanate and a preparation process of tert-butyl isothiocyanate, and belongs to the technical field of preparation of tert-butyl isothiocyanate.
Background
The buprofezin has the chemical name of 2-tert-butylimino-3-isopropyl-5-phenyl-1, 3, 5-thiadiazine-4-ketone and the molecular formula of C 16 H 23 N 3 OS, which was developed by japanese pesticide company for the first time, is a novel selective pesticide for inhibiting the growth and development of insects, has a strong contact killing effect and also has a stomach poisoning effect, and has a mechanism of action of inhibiting chitin synthesis and interfering metabolism of insects, so that nymphs are malformed or adult wings are malformed after desquamation and die slowly. The Chinese medicinal composition can be used for treating the adult with the advantages of obvious effect after being applied for 3-7 days, no direct killing power to the adult, shortened service life, reduced spawning quantity, and produced sterile eggs, and the larvae die quickly even if hatching. The buprofezin has high selectivity, has good control effect on plant hoppers, leafhoppers, whiteflies and hydrocarbon pests of homoptera, and also has lasting larvicide activity on certain coleoptera pests and mites. Can effectively prevent and treat plant hoppers and leafhoppers on rice, tea, leafhoppers on potatoes, oranges and white flies on vegetables, scale insects on oranges and white flies, scale insects on fruit trees and tea trees, and the like. In China, the method has the advantages that,the buprofezin preparation is a commodity name of prometryn and is widely used for paddy rice planting.
Buprofezin is synthesized from two intermediates, N-tert-butyl-N-isopropylthiourea and N-chloromethyl-N-phenylcarbamoyl chloride. The N-tertiary butyl-N-isopropylthiourea is prepared by taking ammonium thiocyanate and tertiary butyl alcohol as initial raw materials, firstly synthesizing a mixture of tertiary butyl thiocyanate and tertiary butyl isothiocyanate, then converting zinc chloride isomerism tertiary butyl thiocyanate into tertiary butyl isothiocyanate, separating isomerism impurities and zinc chloride at high temperature, distilling and purifying to obtain the tertiary butyl isothiocyanate with the content of more than 98%, and then reacting with isopropylamine to obtain the N-tertiary butyl-N-isopropylthiourea. In the process of converting zinc chloride isomerism tert-butyl thiocyanate into tert-butyl isothiocyanate, a high-viscosity substance is generated, and the zinc chloride isomerism tert-butyl thiocyanate has certain fluidity only at high temperature, so that the production environment is very bad and is difficult to process.
Disclosure of Invention
The invention aims to solve the defects in the prior art, and provides a catalyst for preparing tert-butyl isothiocyanate and a preparation process of tert-butyl isothiocyanate, aiming at the problem that high-viscosity substances are generated in the process of converting zinc chloride isomerism tert-butyl thiocyanate into tert-butyl isothiocyanate in the traditional process and influence on production environment.
In order to achieve the above object, the present invention first proposes a catalyst for preparing t-butyl isothiocyanate, which is a dry hydrogen chloride gas.
The invention also provides a preparation process of the tert-butyl isothiocyanate, which comprises the following steps:
according to the mass portions, 70 to 85 portions of ammonium thiocyanate, 200 portions of water, 65 to 90 portions of 85 percent tertiary butanol and 200 to 250 portions of 30 percent hydrochloric acid are taken,
adding ammonium thiocyanate into water, stirring to obtain ammonium thiocyanate solution, adding 85% tertiary butanol into the ammonium thiocyanate solution, heating to 45-50 ℃ to obtain mixed solution, dropwise adding 30% hydrochloric acid into the mixed solution for 30+ -5 min, continuously stirring in the dropwise adding process, stopping stirring, standing and layering, and taking an upper material;
transferring the upper material into a drying container, heating to 50-60 ℃, and then carrying out hydrogen chloride catalytic operation to obtain the tert-butyl isothiocyanate.
Preferably, in the hydrogen chloride catalytic operation, the drying container is vacuumized, and the vacuumized drying container is connected with the dried hydrogen chloride gas, the valve is closed until the drying container is restored to normal pressure, and nitrogen replacement is carried out after 30+/-5 min.
Preferably, the volume of the drying container is 1-1.5 times of the volume of water, and the drying container is vacuumized to 0.08-0.09 MPa.
Preferably, in the hydrogen chloride catalytic operation, a 20% hydrogen chloride dioxane solution is prepared by using dioxane as a solvent, and 4-8 parts of the 20% hydrogen chloride dioxane solution is added into a drying container for 30+/-5 min.
Preferably, stirring is continued for 30-90 min after the completion of the dropwise addition of 30% hydrochloric acid.
The beneficial effects of the invention are mainly as follows:
the dry hydrogen chloride gas is used as the catalyst for preparing the tert-butyl isothiocyanate, the hydrogen chloride is easy to separate and has no byproduct generation, the preparation of the tert-butyl isothiocyanate reaches more than 98 percent, and the preparation environment of the tert-butyl isothiocyanate can be effectively improved.
Detailed Description
The invention provides a catalyst for preparing tert-butyl isothiocyanate and a preparation process of tert-butyl isothiocyanate. The following detailed description of the present invention is provided to facilitate understanding and grasping thereof.
First, a catalyst for preparing tert-butyl isothiocyanate is proposed, which is a dry hydrogen chloride gas. The dry hydrogen chloride gas belongs to the prior art, and more finely, the mass fraction of water in the hydrogen chloride gas<1.0×10 -4 。
The preparation process of the tert-butyl isothiocyanate is described in detail:
according to the mass portion, 70 to 85 portions of ammonium thiocyanate, 200 portions of water, 65 to 90 portions of 85 percent tertiary butanol and 200 to 250 portions of 30 percent hydrochloric acid are taken.
Adding ammonium thiocyanate into water, stirring to obtain ammonium thiocyanate solution, adding 85% tertiary butanol into the ammonium thiocyanate solution, heating to 45-50 ℃ to obtain mixed solution, dropwise adding 30% hydrochloric acid into the mixed solution for 30+ -5 min, continuously stirring in the dropwise adding process, and continuously stirring for 30-90 min after the dropwise adding of 30% hydrochloric acid is completed. Stopping stirring, standing and layering, and taking the upper material.
Transferring the upper material into a drying container, wherein the volume of the drying container is 1-1.5 times of the volume of water, heating to 50-60 ℃, vacuumizing to 0.08-0.09 MPa, introducing dry hydrogen chloride gas into the vacuumizing drying container, recovering normal pressure to the drying container, closing a valve, maintaining for 30+/-5 min, and then performing nitrogen replacement to obtain tert-butyl isothiocyanate.
Example 1
76.1 g of ammonium thiocyanate is added into 200g of water, 87 g of 85% tertiary butyl alcohol is added after stirring and dissolving, the temperature is raised to 45 ℃, 220g of 30% hydrochloric acid is added within 30 minutes, the reflux state is kept for 2 hours, stirring is stopped, the lower water layer is separated still, 96 g of upper material is obtained, and the content of the tertiary butyl thiocyanate is detected to be 54%, and the content of the tertiary butyl isothiocyanate is detected to be 46%.
The materials are transferred into a dry 250 ml flask, the temperature is raised to 50 ℃, the flask is vacuumized to 0.09MPa, a glass tube inserted with the materials is connected into a hydrogen chloride steel bottle, and a valve is opened to restore the pressure in the flask to normal pressure. After 30 minutes of hold, nitrogen was purged. The sample was taken to detect 98.3% t-butyl isothiocyanate.
Example two
95 g of ammonium thiocyanate is added into 250g of water, 87 g of 85% tertiary butyl alcohol is added after stirring and dissolving, the temperature is raised to 45-50 ℃, 250g of 30% hydrochloric acid is added within 30 minutes, the reflux state is kept for 1.5 hours, stirring is stopped, the lower water layer is separated at rest, 105 g of upper material is obtained, and the content of the tertiary butyl thiocyanate is detected to be 51%, and the content of the tertiary butyl isothiocyanate is detected to be 48%.
The materials are transferred into a dry 250 ml flask, the temperature is raised to 55 ℃, the flask is vacuumized to 0.08MPa, a glass tube inserted with the materials is connected into a hydrogen chloride steel bottle, and a valve is opened to restore the pressure in the flask to normal pressure. After 25 minutes of hold, nitrogen was purged. The sample was taken to detect 98.5% t-butyl isothiocyanate.
Example III
76.1 g of ammonium thiocyanate is added into 200g of water, 87 g of 85% tertiary butyl alcohol is added after stirring and dissolving, the temperature is raised to 50 ℃, 250g of 30% hydrochloric acid is added within 30 minutes, the reflux state is kept for half an hour, stirring is stopped, the lower water layer is removed at rest, 97 g of upper material is obtained, and the content of tertiary butyl thiocyanate is detected to be 38%, and the content of tertiary butyl isothiocyanate is detected to be 62%.
The materials are transferred into a dry 250 ml flask, the temperature is raised to 60 ℃, the flask is vacuumized to 0.09MPa, a glass tube inserted with the materials is connected into a hydrogen chloride steel bottle, and a valve is opened to restore the pressure in the flask to normal pressure. After 30 minutes of hold, nitrogen was purged. The sample was taken to detect 98.7% t-butyl isothiocyanate.
Example IV
82.2 g of ammonium thiocyanate is added into 200g of water, 78 g of 85% tertiary butyl alcohol is added after stirring and dissolving, the temperature is raised to 45 ℃, 200g of 30% hydrochloric acid is added within 30 minutes, the reflux state is kept for 1.5 hours, stirring is stopped, the lower water layer is separated still, 94 g of upper material is obtained, and the content of tertiary butyl thiocyanate is detected to be 58%, and the content of tertiary butyl isothiocyanate is detected to be 42%.
Transferring the materials into a dry 250 ml flask, heating to 55 ℃, vacuumizing the flask to 0.09MPa, inserting a glass tube of the materials into a hydrogen chloride steel bottle, opening a valve, and recovering the pressure in the flask to normal pressure. After 30 minutes of hold, nitrogen was purged. The sample was taken to detect 98.6% t-butyl isothiocyanate.
Example five
76.1 g of ammonium thiocyanate is added into 200g of water, 87 g of 85% tertiary butyl alcohol is added after stirring and dissolving, the temperature is raised to 45 ℃, 220g of 30% hydrochloric acid is added within 30 minutes, the reflux state is kept for 2 hours, stirring is stopped, the lower water layer is separated still, 96 g of upper material is obtained, and the content of the tertiary butyl thiocyanate is detected to be 54%, and the content of the tertiary butyl isothiocyanate is detected to be 46%.
The material was transferred to a dry 250 ml flask, heated to 55℃and dried hydrogen chloride was dissolved in dioxane solvent to give a 20% hydrogen chloride dioxane solution, 5g of 20% hydrogen chloride dioxane solution was added to the flask, and the flask was kept for 30 minutes to detect the t-butyl isothiocyanate content of 98.8%.
As can be seen from the above description, the catalyst for preparing tert-butyl isothiocyanate and the preparation process of tert-butyl isothiocyanate of the present invention adopt dry hydrogen chloride gas as the catalyst for preparing tert-butyl isothiocyanate, the hydrogen chloride is easy to separate and no by-product is generated, the preparation of tert-butyl isothiocyanate reaches more than 98%, and the preparation environment of tert-butyl isothiocyanate can be effectively improved.
While the foregoing has been described in terms of embodiments of the present invention, it will be appreciated that the embodiments of the invention are not limited by the foregoing description, but rather, all embodiments of the invention may be modified in structure, method or function by one skilled in the art to incorporate the teachings of this invention, as expressed in terms of equivalent or equivalent embodiments, without departing from the scope of the invention.

Claims (3)

1. The preparation process of the tert-butyl isothiocyanate is characterized by comprising the following steps:
according to the mass portions, 70 to 85 portions of ammonium thiocyanate, 200 portions of water, 65 to 90 portions of 85 percent tertiary butanol and 200 to 250 portions of 30 percent hydrochloric acid are taken,
adding ammonium thiocyanate into water, stirring to obtain ammonium thiocyanate solution, adding 85% tertiary butanol into the ammonium thiocyanate solution, heating to 45-50 ℃ to obtain mixed solution, dropwise adding 30% hydrochloric acid into the mixed solution for 30+ -5 min, continuously stirring in the dropwise adding process, stopping stirring, standing and layering, and taking an upper material;
transferring the upper material into a drying container, heating to 50-60 ℃, and then carrying out dry hydrogen chloride catalytic operation to obtain tert-butyl isothiocyanate, wherein the mass fraction of water in the hydrogen chloride gas<1.0×10 -4 ；
In the hydrogen chloride catalytic operation, the drying container is vacuumized, and the vacuumized drying container is connected with dry hydrogen chloride gas until the drying container is recovered to normal pressure, the valve is closed, and nitrogen replacement is carried out after 30+/-5 min.
2. The process for preparing tert-butyl isothiocyanate according to claim 1, wherein:
the volume of the drying container is 1 to 1.5 times of the volume of water, and the drying container is vacuumized to 0.08 to 0.09MPa.
3. The process for preparing tert-butyl isothiocyanate according to claim 1, wherein:
and continuously stirring for 30-90 min after the dropwise adding of 30% hydrochloric acid is completed.
CN202010403496.2A 2020-05-13 2020-05-13 Catalyst and preparation process of tert-butyl isothiocyanate Active CN111450857B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010403496.2A CN111450857B (en) 2020-05-13 2020-05-13 Catalyst and preparation process of tert-butyl isothiocyanate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010403496.2A CN111450857B (en) 2020-05-13 2020-05-13 Catalyst and preparation process of tert-butyl isothiocyanate

Publications (2)

Publication Number Publication Date
CN111450857A CN111450857A (en) 2020-07-28
CN111450857B true CN111450857B (en) 2023-06-13

Family

ID=71672341

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010403496.2A Active CN111450857B (en) 2020-05-13 2020-05-13 Catalyst and preparation process of tert-butyl isothiocyanate

Country Status (1)

Country Link
CN (1) CN111450857B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112774606A (en) * 2020-12-24 2021-05-11 安道麦安邦(江苏)有限公司 Production method and equipment of high-purity buprofezin intermediate 1-isopropyl-3-tert-butylthiourea
CN113751205A (en) * 2021-09-10 2021-12-07 紫金矿业集团股份有限公司 N-tert-butyl ester collecting agent and preparation method thereof

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1092785A (en) * 1992-12-04 1994-09-28 希巴-盖吉股份公司 Oligomeric HALS phosphorous acid ester and HALS phosphinate with used as stabilizers
CA2207953A1 (en) * 1996-06-28 1997-12-28 Randall Wayne Stephens Process for the manufacture of acetonylbenzamides
CN101245160A (en) * 2008-03-11 2008-08-20 四川大学 Fire retardant thermoplastic resin composition and manufacture method thereof
JP2011195584A (en) * 2010-02-26 2011-10-06 Mitsui Chemicals Inc Transition metal complex compound, olefin polymerizing catalyst containing the compound, and method for producing olefin polymer which is carried out in the presence of the catalyst
CN102241573A (en) * 2010-05-10 2011-11-16 陕西唐正科技发展有限公司 Preparation method of 3,3-methyl butyraldehyde
WO2014017447A1 (en) * 2012-07-25 2014-01-30 昭和電工株式会社 Membrane electrode assembly and fuel cell provided with same
CN103755612A (en) * 2013-12-20 2014-04-30 浙江普康化工有限公司 Method for synthesizing phenyl isothiocyanate
CN104177473A (en) * 2014-08-20 2014-12-03 山东奔月生物科技有限公司 Synthesis method of neotame
CN110446696A (en) * 2017-03-24 2019-11-12 三井化学株式会社 The manufacturing method of multi-thiol compound, polymerizable composition, polymerizable composition and application thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08333258A (en) * 1994-12-14 1996-12-17 Japan Tobacco Inc Thiazine or thiazepine derivative and nitrogen monoxide synthetase inhibitor containing the compound
US8173642B2 (en) * 2005-10-25 2012-05-08 Shionogi & Co., Ltd. Aminodihydrothiazine derivatives

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1092785A (en) * 1992-12-04 1994-09-28 希巴-盖吉股份公司 Oligomeric HALS phosphorous acid ester and HALS phosphinate with used as stabilizers
CA2207953A1 (en) * 1996-06-28 1997-12-28 Randall Wayne Stephens Process for the manufacture of acetonylbenzamides
CN101245160A (en) * 2008-03-11 2008-08-20 四川大学 Fire retardant thermoplastic resin composition and manufacture method thereof
JP2011195584A (en) * 2010-02-26 2011-10-06 Mitsui Chemicals Inc Transition metal complex compound, olefin polymerizing catalyst containing the compound, and method for producing olefin polymer which is carried out in the presence of the catalyst
CN102241573A (en) * 2010-05-10 2011-11-16 陕西唐正科技发展有限公司 Preparation method of 3,3-methyl butyraldehyde
WO2014017447A1 (en) * 2012-07-25 2014-01-30 昭和電工株式会社 Membrane electrode assembly and fuel cell provided with same
CN103755612A (en) * 2013-12-20 2014-04-30 浙江普康化工有限公司 Method for synthesizing phenyl isothiocyanate
CN104177473A (en) * 2014-08-20 2014-12-03 山东奔月生物科技有限公司 Synthesis method of neotame
CN110446696A (en) * 2017-03-24 2019-11-12 三井化学株式会社 The manufacturing method of multi-thiol compound, polymerizable composition, polymerizable composition and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
黄金艳 ; .2-氯-5-氯甲基-1,3-噻唑的合成.河北化工.2010,(第08期),11-14. *

Also Published As

Publication number Publication date
CN111450857A (en) 2020-07-28

Similar Documents

Publication Publication Date Title
CN111450857B (en) Catalyst and preparation process of tert-butyl isothiocyanate
Agrawal et al. Models for studying rice crop-weather relationship
CN101579024A (en) Artificial inoculation production method of camellia nitidissima
CN114853651B (en) Method for synthesizing liquid sodium N-methyldithiocarbamate by micro-channel reactor
CN101362786B (en) Method for preparing ivermectin
CN103922951A (en) Method for extracting leucine by utilizing corn protein powder
WO2008064547A1 (en) The method of producing ethanol from dried sweet stem corn or sweet sorghum stalks
CN109705048B (en) Clean preparation method of tebuconazole
US20220048877A1 (en) Process for the production of furfural
CN108714312A (en) A kind of oil tea shell rises in value the method utilized at many levels
CN104803879A (en) Preparation technology of methoxyfenozide
CN107311922A (en) A kind of synthetic method of third pyrrole ether
CN105503680B (en) The method for improving Cupric sulfate centrifuge mother liquor flour extraction
CN109336848B (en) Tebuconazole intermediate and preparation method of tebuconazole
WO2020174399A1 (en) A feed ingredient comprising butyrate and a selected fermentation product
TWI596092B (en) Processes for preparing 5-(chloromethyl)furfural
CN114262359A (en) Preparation method of carfilzomib impurities
CN113368896A (en) Catalyst for diflubenzuron synthesis and preparation method of diflubenzuron
CN110178845B (en) Growth-promoting disease-resistant organic rare earth compound and preparation method and application thereof
CN106365980A (en) Method for preparing anhydrous sodium acetate
CN112674097A (en) Chitosan oligosaccharide and S-abscisic acid compound sterilization regulator and preparation method thereof
CN109804746A (en) A kind of field sand Carbon fixation method
CN106244184B (en) A kind of method that pyrolysis gas of biomass catalytic pyrolysis prepares BTX
CN101273720A (en) Method for preparing raw medicament of stable fenpyroximate
CN110981750A (en) Method for synthesizing 2-pentanone oxime from 2-pentanone through ammoxidation

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20230620

Address after: 215314 No. 508, Huangpujiang North Road, Zhoushi Town, Kunshan City, Suzhou City, Jiangsu Province

Patentee after: Jiangsu zaitou Biotechnology Co.,Ltd.

Address before: Room 306, Building 3, Dongchuang Technology Center, Qianjin East Road Enterprise Science Park, Kunshan Development Zone, Suzhou City, Jiangsu Province, 215300

Patentee before: Jiangsu parrini New Material Technology Co.,Ltd.