Epichlorohydrin
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A New Approach to Prepare Polyethylene Glycol Allyl Glycidyl Ether
E3S Web of Conferences 267, 02004 (2021) https://doi.org/10.1051/e3sconf/202126702004 ICESCE 2021 A new approach to prepare Polyethylene Glycol Allyl Glycidyl Ether Huizhen Wang1*, Ruiyang Xie1, Mingjun Chen1*, Weihao Deng1, Kaixin Zhang2, Jiaqin Liu1 1School of Science, Xihua University, Chengdu 610039, China; 2Chengdu Jingyiqiang Environmental Protection Technology Co., Ltd. Abstract. The polyethylene glycol allyl glycidyl ether (PGAGE) is an important intermediate for preparing silicone softener that can be synthesized from allyl alcohol polyoxyethylene ether and epichlorohydrin (ECH). The performance parameters including the concentration of ECH, initial boron trifluoride diethyl etherate (BFEE) as well as CaCl2 quality were investigated respectively. The optimum process parameters which can get high capping and low by-product rate are as follows: the ECH concentration is 2.0 M, the initial BFEE concentration is 1.65mM, and the CaCl2 dosage is 1.65g/L. Under these conditions, the maximal yield can be improved to 91.36%, the percent of capping rate is higher than 98.16%, the residual concentration of F- is only 0.63 mg/L. concentrated basic solution, in which the total yield was between 90%~91% by Matsuoka et al. [10] also use the 1 Introduction two-step reaction to synthesize AGE based on the reaction Polyethylene glycol allyl glycidyl ether (PGAGE) and the of allyl alcohol with ECH using BFEE as the catalyst. allyl polyoxyethylene ether (APEG), tethering with both Their results demonstrated that the yield reaches 82% alkene and epoxy groups, are widely used as fabric under the following condition: n (ECH) : n (allyl alcohol): finishing agent [1-2] , reactive diluent [3] , cross-linking (catalysis) = 1: (1~3) : (0.01~0.002). -
A New Coupling Process for Synthesis of Epichlorohydrin from Dichloropropanols
2nd International Conference on Machinery, Materials Engineering, Chemical Engineering and Biotechnology (MMECEB 2015) A new coupling process for synthesis of epichlorohydrin from dichloropropanols Dawei Wu, Sumin Zhou* School of Chemical Engineering, Huaiyin Institute of Technology, Huaian 223005, China [email protected] Keywords: dichloropropanol, epichlorohydrin, tubular reactor, wiped film evaporation. Abstract. As an important material used in the production of epoxy resins, epichlorohydrin is usually derived from the saponification and cyclization of dichloropropanol in a tower reacting system. In order to reduce energy consumption and wastewater discharge, a new process of tubular reactor coupled with wiped film evaporation was adopt to produce epichlorohydrin. The effects of different technological parameters on the yield of the coupling process were investigated, such as reactants' molar ratio, reaction & evaporation temperature, residence time and so on. Results indicated that the use of coupling process will significantly reduce the material consumption and shorter the reaction time. This coupling process provided a useful suggestion for the design of the industrial plants. 1. Introduction Epichlorohydyin(ECH), also known as 1-chloro-2, 3-epoxy propane, is an important chemical material, mainly used to synthesizing epoxy resin, chlorohydrins rubber, pesticide, plasticizer and so on [1]. The main method to produce ECH is high-temperature chlorination of propylene [2]. With the fast-development of biodiesel production, the use of glycerol for producing ECH [3-4] is going to mature and has become an important industrial technological process [5]. Although the difference raw materials were used, the processes also consist of two reaction steps as well. First step is the saponification and cyclization of dichloropropanol (DCP) to produce ECH. -
Production of Glycidyl Compounds
Office europeen des brevets (fi) Publication number : 0 491 529 A1 @ EUROPEAN PATENT APPLICATION @ Application number : 91311630.7 © Int. CI.5: C07D 301/28, C07D 303/24 (22) Date of filing : 13.12.91 (30) Priority : 18.12.90 GB 9027448 (72) Inventor : Thoseby, Michael Robert 29 De Freville Avenue Cambridge (GB) (43) Date of publication of application : Inventor : Rolfe, William Martin 24.06.92 Bulletin 92/26 42 Vetch Walk Haverhill, Suffolk (GB) (S) Designated Contracting States : CH DE ES FR GB IT LI NL (74) Representative : Sparrow, Kenneth D. et al CIBA-GEIGY PLC. Patent Department, Central Research, Hulley Road @ Applicant : CIBA-GEIGY AG Macclesfield, Cheshire SK10 2NX (GB) Klybeckstrasse 141 CH-4002 Basel (CH) (54) Production of glycidyl compounds. (57) A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to pro- duce the 1:1 adduct, in the presence, as catal- yst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IMA of the Periodic Table of Elements (according to the IUPAC 1970 convention) ; and then dehydrochlorinating the product so obtained. CM LU Jouve, 18, rue Saint-Denis, 75001 PARIS 1 EP 0 491 529 A1 2 The present invention relates to a process for the 100 parts by weight of the alcohol reactant. production of glycidyl compounds. The alcohol reactant may be a primary, secon- The addition reaction between epoxides and dary or tertiary alcohol. While monohydric alcohols alcohols, in the presence of a catalyst, to produce an may be used, e.g. -
Gasket Chemical Services Guide
Gasket Chemical Services Guide Revision: GSG-100 6490 Rev.(AA) • The information contained herein is general in nature and recommendations are valid only for Victaulic compounds. • Gasket compatibility is dependent upon a number of factors. Suitability for a particular application must be determined by a competent individual familiar with system-specific conditions. • Victaulic offers no warranties, expressed or implied, of a product in any application. Contact your Victaulic sales representative to ensure the best gasket is selected for a particular service. Failure to follow these instructions could cause system failure, resulting in serious personal injury and property damage. Rating Code Key 1 Most Applications 2 Limited Applications 3 Restricted Applications (Nitrile) (EPDM) Grade E (Silicone) GRADE L GRADE T GRADE A GRADE V GRADE O GRADE M (Neoprene) GRADE M2 --- Insufficient Data (White Nitrile) GRADE CHP-2 (Epichlorohydrin) (Fluoroelastomer) (Fluoroelastomer) (Halogenated Butyl) (Hydrogenated Nitrile) Chemical GRADE ST / H Abietic Acid --- --- --- --- --- --- --- --- --- --- Acetaldehyde 2 3 3 3 3 --- --- 2 --- 3 Acetamide 1 1 1 1 2 --- --- 2 --- 3 Acetanilide 1 3 3 3 1 --- --- 2 --- 3 Acetic Acid, 30% 1 2 2 2 1 --- 2 1 2 3 Acetic Acid, 5% 1 2 2 2 1 --- 2 1 1 3 Acetic Acid, Glacial 1 3 3 3 3 --- 3 2 3 3 Acetic Acid, Hot, High Pressure 3 3 3 3 3 --- 3 3 3 3 Acetic Anhydride 2 3 3 3 2 --- 3 3 --- 3 Acetoacetic Acid 1 3 3 3 1 --- --- 2 --- 3 Acetone 1 3 3 3 3 --- 3 3 3 3 Acetone Cyanohydrin 1 3 3 3 1 --- --- 2 --- 3 Acetonitrile 1 3 3 3 1 --- --- --- --- 3 Acetophenetidine 3 2 2 2 3 --- --- --- --- 1 Acetophenone 1 3 3 3 3 --- 3 3 --- 3 Acetotoluidide 3 2 2 2 3 --- --- --- --- 1 Acetyl Acetone 1 3 3 3 3 --- 3 3 --- 3 The data and recommendations presented are based upon the best information available resulting from a combination of Victaulic's field experience, laboratory testing and recommendations supplied by prime producers of basic copolymer materials. -
Material Safety Data Sheet Allyl Chloride MSDS
He a lt h 2 3 Fire 3 1 3 Re a c t iv it y 0 Pe rs o n a l Pro t e c t io n H Material Safety Data Sheet Allyl Chloride MSDS Section 1: Chemical Product and Company Identification Product Name: Allyl Chloride Contact Information: Catalog Codes: 10058 Finar Limited 184-186/P, Chacharwadi Vasna, CAS#: 107-05-1 Sarkhej-Bavla Highway, Ta.: Sanand, Dist.: Ahmedabad, RTECS: UC7350000 Email: [email protected] TSCA: TSCA 8(b) inventory: Allyl Chloride Web: www.finarchemicals.com CI#: Not available. Synonym: 3-Chloropropene; 3-Chloroprene Chemical Name: Allyl Chloride Chemical Formula: Not available. Section 2: Composition and Information on Ingredients Composition: Name CAS # % by Weight Allyl Chloride 107-05-1 100 Toxicological Data on Ingredients: Allyl Chloride: ORAL (LD50): Acute: 460 mg/kg [Rat]. 425 mg/kg [Mouse]. DERMAL (LD50): Acute: 2066 mg/kg [Rabbit]. VAPOR (LC50): Acute: 11000 mg/m 2 hours [Rat]. 5800 mg/m 3 2 hours [Guinea pig]. Section 3: Hazards Identification Potential Acute Health Effects: Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation. Slightly hazardous in case of skin contact (permeator). Severe over-exposure can result in death. Potential Chronic Health Effects: CARCINOGENIC EFFECTS: Classified A3 (Proven for animal.) by ACGIH, 3 (Equivocal evidence.) by NTP, C (Possible for human.) by EPA. Classified None. by OSHA, None. by NIOSH. 3 (Not classifiable for human.) by IARC. MUTAGENIC EFFECTS: Mutagenic for bacteria and/or yeast. TERATOGENIC EFFECTS: Not available. DEVELOPMENTAL TOXICITY: Not available. The substance may be toxic to kidneys, lungs, liver, upper respiratory tract, skin, eyes. -
Increasing the Production of 3-Chloro-1-Propene (Allyl Chloride) in Unit 600
Increasing the Production of 3-Chloro-1-Propene (Allyl Chloride) in Unit 600 Background You are currently employed by the TBWS Corp. at their Beaumont, Texas plant, and you have been assigned to the allyl chloride facility. A serious situation has developed at the plant, and you have been assigned to assist with troubleshooting the problems which have arisen. Recently your sister plant in Alabama was shut down by the EPA (Environmental Protection Agency) for violations concerning sulfur dioxide emissions from a furnace in their allyl chloride facility. Fortunately, the Beaumont facility had switched to natural gas as a fuel for their process in the early 1990s and, hence, is currently in compliance with the EPA and Texas regulations. However, the loss of the Alabama plant, albeit for a short time only, has put considerable pressure on the Beaumont plant to fulfill contractual obligations to our customers in Alabama for allyl chloride. Thus, part of your assignment is to advise management concerning the increase in production of allyl chloride that can be made at the Beaumont facility. Another related issue which has been discussed by management is the long term profitability of both allyl chloride facilities. Allyl chloride is used as a precursor in the production of allyl alcohol, glycerin, and a variety of other products used in the pharmaceutical industry. More efficient plants have been built recently by our competitors and we are being slowly squeezed out of the market by these rival companies. We still maintain a loyal customer base due to our excellent technical and customer service departments and our aggressive sales staff. -
Cl2-1,5-Hexadiene from Reaction of Allyl Chloride and K2ptcl4
UC San Diego UC San Diego Previously Published Works Title Unexpected synthesis and structural characterization of Pt(II)Cl2-1,5-hexadiene from reaction of allyl chloride and K2PtCl4 Permalink https://escholarship.org/uc/item/3s82k79p Journal Inorganica Chimica Acta, 364(1) ISSN 00201693 Authors Nair, Reji N Golen, James A Rheingold, Arnold L et al. Publication Date 2010-12-01 DOI 10.1016/j.ica.2010.09.006 Peer reviewed eScholarship.org Powered by the California Digital Library University of California Inorganica Chimica Acta 364 (2010) 272–274 Contents lists available at ScienceDirect Inorganica Chimica Acta journal homepage: www.elsevier.com/locate/ica Note Unexpected synthesis and structural characterization of Pt(II)Cl2-1,5-hexadiene from reaction of allyl chloride and K2PtCl4 ⇑ Reji N. Nair a, James A. Golen b,c, Arnold L. Rheingold b, Douglas B. Grotjahn a, a Department of Chemistry and Biochemistry, 5500 Campanile Drive, San Diego State University, San Diego, CA 92182-1030, United States b Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, United States c Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, United States article info abstract Article history: An unexpected, new and convenient synthetic procedure for the synthesis of Pt(II)Cl2-1,5-hexadiene is Available online 21 September 2010 reported which is done under mild conditions, including a very short reaction time of 10 min. The com- plex was isolated and crystallized, leading to the first reported crystal structure of the diene complex. Dedicated to Professor Arnold L. -
Comparisons of Epoxy Technology for Protective Coatings and Linings In
ComparisonsComparisons ofof EpoxyEpoxy TechnologyTechnology forfor ProtectiveProtective CoatingsCoatings andand LiningsLinings inin WastewaterWastewater FacilitiesFacilities By John D. Durig, General Polymers, Cincinnati, Ohio, USA Aeration tank at a wastewater plant. Bis F epoxy resin with an aliphatic or a cycloaliphatic amine curing agent is appropriate. Editor’s Note: This article was first presented at SSPC (Photos courtesy of the author) 99, The Industrial Protective Coatings Conference and Exhibit, November 14-18, 1999, in Houston, TX, USA, and published in The Proceedings of the Seminars, SSPC 99-14, pp. 31-37. poxy technology and methods of curing and Epoxy Resin Technology E reacting with amine-based hardeners have There are three types of epoxy resins that find application continued to evolve since the first epoxy patents were is- in wastewater treatment facilities: bisphenol A, bisphenol sued in the 1930s. The possible reactions combined with F, and novolac resins. These resins all result from reac- wide-ranging formulation additives have resulted in a myri- tions of epichlorohydrin with phenolic compounds. The ad of products that can easily confuse decision makers type and number of phenolic groups determine both when it comes to product selection. Adding to the confu- physical and performance properties of the cured resin. sion is the wide range of environmental factors that must be considered when choosing a protective coating system. Bisphenol A Resin Structure This article will identify the primary differences be- Bisphenol A is a reaction product of phenol and acetone. tween three types of epoxies and four types of amine- Bisphenol A is reacted with epichlorohydrin to form based hardeners typically used in coatings for wastewater diglycidylether bisphenol A resin or DGEBA. -
Separation of a Multicomponent System Formed in the Production of Epichlorohydrin*
THEORETICAL BASES OF CHEMICAL TECHNOLOGY Separation of a Multicomponent System Formed in the Production of Epichlorohydrin* E.A. Okhlopkova@, L.A. Serafimov, A.V. Frolkova, P.P. Tsekin Moscow Technological University (Institute of Fine Chemical Technologies), Moscow, 119571 Russia @ Corresponding author e-mail: [email protected] Epichlorohydrin is an important product of the basic organic synthesis. One promising direction of epichlorohydrin manufacturing is the liquid-phase epoxidation of allyl chloride with an aqueous solution of hydrogen peroxide in an organic solvent, methanol, in the presence of a heterogeneous catalyst, a titanium-containing zeolite. The multicomponent system of epichlorohydrin production according to this method contains allyl chloride, methanol, water, epichlorohydrin, 3-chloro-1,2-propanediol, 3-chloro-1-methoxypropanol-2 and hydrogen peroxide. In this work the thermodynamic topological analysis of the phase diagram of this multicomponent system of epichlorohydrin production was performed. On the basis of this study a principal technological scheme of separation of the studied system containing five distillation columns and a Florentine vessel was proposed. Keywords: epichlorohydrin, phase equilibrium, mathematical simulation, separation complex. Introduction Epichlorohydrin is an important product of the basic organic synthesis. It is used for producing a number of products that are applied in different industries. Epichlorohydrin contains an active epoxy group and a labile chlorine atom. Due to this it easily enters various reactions of electrophilic and nucleophilic addition and substitution. Paints, glues, ion exchange resins, synthetic fibers and rubbers characterized by high thermal stability and gas-tightness [1] are produced on its basis. About 80% of products based on epichlorohydrin are used for obtaining epoxy resins [2]. -
Allyl Chloride
ENEA0070 - ALLYL CHLORIDE ALLYL CHLORIDE Safety Data Sheet ENEA0070 Date of issue: 06/25/2015 Version: 1.0 SECTION 1: Identification of the substance/mixture and of the company/undertaking 1.1. Product identifier Product form : Substance Physical state : Liquid Substance name : ALLYL CHLORIDE Product code : ENEA0070 Formula : C3H5Cl Synonyms : 3-CHLOROPROPENE; 2-PROPENYL CHLORIDE Chemical family : ESTER 1.2. Relevant identified uses of the substance or mixture and uses advised against Use of the substance/mixture : Chemical intermediate For research and industrial use only 1.3. Details of the supplier of the safety data sheet GELEST, INC. 11 East Steel Road Morrisville, PA 19067 USA T 215-547-1015 - F 215-547-2484 - (M-F): 8:00 AM - 5:30 PM EST [email protected] - www.gelest.com 1.4. Emergency telephone number Emergency number : CHEMTREC: 1-800-424-9300 (USA); +1 703-527-3887 (International) SECTION 2: Hazards identification 2.1. Classification of the substance or mixture Classification (GHS-US) Flam. Liq. 3 H226 Acute Tox. 3 (Oral) H301 Acute Tox. 4 (Inhalation:vapour) H332 Skin Irrit. 2 H315 Eye Irrit. 2A H319 Aquatic Acute 3 H402 Full text of H-phrases: see section 16 2.2. Label elements GHS-US labeling Hazard pictograms (GHS-US) : GHS02 GHS06 GHS07 Signal word (GHS-US) : Danger Hazard statements (GHS-US) : H226 - Flammable liquid and vapor H301 - Toxic if swallowed H315 - Causes skin irritation H319 - Causes serious eye irritation H332 - Harmful if inhaled H402 - Harmful to aquatic life Precautionary statements (GHS-US) : P210 - Keep -
The Production of Epichlorohydrin from Glycerol. a Bachelor Integration Project for Delfzijl’S Chempark
The production of epichlorohydrin from glycerol. A Bachelor Integration Project for Delfzijl’s Chempark Ruurd Feikes van der Heide University of Groningen Faculty of Science and Engineering IE&M Bachelor Thesis Supervisor 1: prof. Dr. Ir. HJ (Erik) Heeres Supervisor 2: Dr. Ing. H. Kloosterman Syncom supervisor: Dr. Ir. Andre Heeres June 2018 Pelsterstraat 32 9711 KM Groningen (06) 13787270 [email protected] student number 2674122 1 Table of content Introduction (RDP) -Problem context -Stakeholder analysis -System description -Goal statement -Design goal -Scope -Research questions -Cycle choice Abstract Backgrounds -Glycerol -Epichlorohydrin Benchmark -Propylene into epichlorohydrin, via allyl chloride -Allyl chloride to epichlorohydrin -TRL Innovation - Glycerol into epichlorohydrin -Hydrochlorination -Hexanoic acid -Acetic acid -Dehydrochlorination -TRL Cost analysis -Hexanoic acid -Solid oxide Discussion and conclusions References Appendix 2 Problem context The city of Delfzijl (Netherlands) has a chemical park with multiple factories present. The companies at the chemical park have interrelationships with each other which results that if a few of them stop producing products, the other companies will find problems in their own existence. The committee Willems started an investigation how the chemical park should optimize its competitiveness among the business environment nowadays. Willems used to be a high ranked employee of Shell before leaving the company. The committee stated that if the companies on the park want to stay in business, changes within production methods have to be made. A more sustainable production method where green raw materials like biomass are converted into valuable products is the solution to stay competitive. Prof. Dr. Ir. -
Risk Based Design of Allyl Chloride Production Plant Alba Turja*, Micaela Demichela
Risk Based Design of Allyl Chloride Production Plant Alba Turja*, Micaela Demichela Department of Material Science and Chemical Engineering, SAfeR Research Group, Polytechnic of Turin C.so Duca degli Abruzzi, 24 10129 Turin [email protected] The necessity to identify and quantify the risks for men and the environment, but also the excessive consumption of resources and energy related to the process plants has led to the formulation of analytical methods capable of assessing the reliability and availability of these systems in order to optimize their operation. Integrated Dynamic Decision Analysis (I.D.D.A.), in particular, represents a tool for the logic modeling of the process plants based on “dynamic” event trees able to describe the system both as “logic” concatenation of events and “probabilistic” coherence. This approach was used for reviewing the design of a plant for the production of allyl chloride by chlorination of propylene in exothermic conditions. This paper aims at building an objective and documented reference for the decision making about the design altrenatives to be adopted for risk minimization. 1. Introduction In order to have guarantees of consistency and completeness in a risk assessment used as a basis for a proper plant design, the probabilistic model of the system should be completed with a phenomenological interface of the process. This approach was used for reviewing the design of a plant for the production of allyl chloride by chlorination of propylene in exothermic conditions. The allyl chloride is product by the chlorination of propylene at high temperature: CH2=CH-CH3 + Cl2 CH2=CH-CH2Cl + HCl (1) r1= 3301562 exp (-15118/RT) p p ; reaction velocity [kmole /h m³] C3 H 6 Cl2 Cl2 ,reacted CH2=CH-CH3 + Cl2 CH2Cl-CHCl-CH3 (2) r2= 185,5 exp (-13811/RT) p p ; reaction velocity [kmole /h m³] C3 H 6 Cl2 Cl2 ,reacted At these temperatures (300-600°C), the chlorination occurs through a radical mechanism where the hydrogen atom in allylic position is replaced preferentially by chlorine giving rise to allyl chloride.