CN105924415A - Method for producing alkenyl succinic anhydride - Google Patents

Method for producing alkenyl succinic anhydride Download PDF

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Publication number
CN105924415A
CN105924415A CN201610220253.9A CN201610220253A CN105924415A CN 105924415 A CN105924415 A CN 105924415A CN 201610220253 A CN201610220253 A CN 201610220253A CN 105924415 A CN105924415 A CN 105924415A
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China
Prior art keywords
carbon
reaction
constant temperature
internal olefin
accordance
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Inventor
高文艺
梁相程
王锐
任立国
张晓丽
王心悦
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Liaoning Shihua University
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Liaoning Shihua University
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Priority to CN201610220253.9A priority Critical patent/CN105924415A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14—Carboxylic acids; Derivatives thereof
    • D21H17/15—Polycarboxylic acids, e.g. maleic acid
    • D21H17/16—Addition products thereof with hydrocarbons
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents

Abstract

The invention discloses a method for producing alkenyl succinic anhydride. The method is as below: preheating reaction materials in a reaction kettle, completely melting; first heating to 125 to 180 DEG C, reacting at a constant temperature for a period of time, then continuing heating to 190 to 230 DEG C, and optionally insulating for a period of time until the end of the reaction. The method has reasonable process; the added middle constant temperature reaction section increases the fully mixing of the reactants and the degree of effective reaction, so as to effectively reduce the occurrence of side reaction, and greatly improve the purity and color of the product.

Description

A kind of method producing alkenyl succinic anhydride
Technical field
The present invention relates to the process of a kind of new and effective production ASA (alkenyl succinic anhydride).
Background technology
Paper industry is the chemical process industry (CPI) with fiber as raw material, in slurrying, bleaches, pulls an oar, manufactures paper with pulp And each stage of one-tenth this technique overall process of paper conversion, all it be unable to do without the application of various chemicals.They Have can give the various special superior function of paper (as water-resistance, grease resistance, wet strength, flatness, Printability, flexibility etc.), the fibrous raw material making employing poor produce thinner, more in vain, more firm Paper be possibly realized；Can make production process optimization, the paper machine operation speed that have improve, and the most significantly subtract Few environmental pollution, brings good economic benefit to paper industry.
China's paper chemicals industry is started late, and to 20th century the mid-80, just starts progressively Development.1986 Technology Bureaus of Nian Yuan the Ministry of Chemical Industry, papermaking office of former China National Light Industrial Products Department have held the whole nation in Hangzhou united organization Papermaking chemical product technology forum, can on propose and accelerate exploitation and the application of China's papermaking chemical product, add The strengthening work demand for development worked hard in glove with and cooperate interdepartmental with papermaking two.By 1994, China's paper chemistry The exploitation of product there has been with production and develops faster, as various novel sizing agents, dry (wet) reinforcing agent, Retention (filter) agent, dispersant, flocculant, defoamer, lubricant, coating adhesive, waterproofing agent, Fire retardant, softening agent, waste paper deinking agent etc., through studying, develop, producing, obtain in paper plant It is widely applied.
In pulping and paper-making production process add chemicals, a class belongs to basic chemical raw materials, as Caustic soda, Alumina etc.；Another kind of, it is addition less pulping and paper making chemistry auxiliary agent.The latter is pulping and papermaking processes In in order to improve some characteristic of paper pulp or paper, reduce supplies consumption and improve operating condition etc., to master The general name of a small amount of chemical substance added in material.The most also pulping and paper making chemistry auxiliary agent is referred to as papermaking Product.Papermaking chemical product presses paper-making process classification, can be divided into pulping chemical, copy paper chemicals and add Work paper chemicals three major types.Wherein copy paper chemicals includes: internal sizing agent, Cypres, humidification Strong agent, drying strengthening agent, fluidizer filter aid, paper softener, dispersing agent for fibre, paper dyestuff, fluorescence increase White agent, felt abluent etc..Wherein internal sizing agent refers to that sizing agent makes an addition in paper pulp, executes to play Glue effect, typically have Colophonium saponification glue, Pexol, dispersion rosin size (Dispersed Anionic Rosin Size, Cationic dispersion rosin size), alkyl ketene dimer (AKD) and alkenyl succinic anhydride (ASA) isoreactivity Sizing agent, petroleum resin sizing agent etc..
ASA is in modern paper industry, produces the neutral sizing agent used by fine paper.In current papermaking Industry, neutral sizing has become as the main flow of technology development.In neutral sizing agent, topmost product is exactly AKD and ASA.Both sizing agents, due to its respective feature, all obtain in paper industry at home and abroad It is widely applied.ASA is fast due to its lower machine ripening, the spies such as absolute dosage is little, and on-the-spot emulsifying technology is ripe Point, is the most progressively more widely used.Particularly in painting processing paper field, owing to body paper produces To be coated processing afterwards at once, so, the feature of ASA has obtained sufficiently sending out in painting processing paper Wave, and obtained the generally accreditation of industry.But, due to ASA on-the-spot emulsifying device substantially by External papermaking chemical product company provides, and cost is higher.And, ASA raw materials for production at home mainly by Import meets, and does not use suitable catalyst, and productivity is relatively low, and cost is high.So for some The papermaking enterprise that scale is less, the interest of ASA supplier is little.Entirety along with China's papermaking enterprise scale Improving, or the production domesticization of ASA emulsifying device is to reduce the threshold using ASA, ASA sizing agent is bound to China's paper industry is occupied more importantly position.
In prior art, with C13-C14Interior alkene and maleic anhydride be raw material, prepare alkenyl succinic anhydride (ASA), under current process conditions product yield less than 55%.Further, and due to operating condition not Enough perfect, often cause side reaction to increase, product purity reduces, and outward appearance and color and luster are poor.
Summary of the invention
For the deficiencies in the prior art, it is an object of the invention to provide the work of a kind of new and effective production ASA Process.
A kind of method producing alkenyl succinic anhydride (ASA) of the present invention, including herein below:
A) carbon 13 internal olefin and carbon 14 internal olefin are mixed to form mixtures of internal olefins, described carbon 13 Internal olefin and carbon 14 internal olefin are the linear internal of carbon number 13～14, alkene in described carbon 13 The mass ratio of hydrocarbon and carbon 14 internal olefin is 1.5:1～8:1；
B) by the mixtures of internal olefins of step a) and maleic anhydride according to the mol ratio of 1.5:1～8:1 Uniformly mixing；
C) obtained by step b), mixing raw material is warming up to 50～120 DEG C, and constant temperature more than 0.5 hour makes Reaction raw materials is completely melt；
D) step c) gained initial mixture is warming up to 125～180 DEG C, and constant temperature at this temperature Reaction a period of time；
E), after 125～180 DEG C of constant temperature terminate, continue reaction temperature to be warming up to 190～230 DEG C, optionally Constant temperature a period of time, reaction terminates；
F) step e) gained product is through separating, and obtains alkenyl succinic acid anhydride product.
In the method for the present invention, in step a), the purity of carbon 13 internal olefin and carbon 14 internal olefin is More than 80%, preferably more than 95%.The mass ratio of described carbon 13 internal olefin and carbon 14 internal olefin is preferably 2:1～5:1.
In step b), mixtures of internal olefins and preferred 2:1～5:1 of mol ratio of maleic anhydride.
In the method for the present invention, wherein the time of the described constant temperature of step c) is more than 0.1 hour, is preferably 0.1～2 hour, so that reaction raw materials is completely melt.
In the method for the present invention, the heating rate in step c) is generally 0.5～20 DEG C/h, preferably 1～ 5℃/h。
In the method for the present invention, the heating rate in step d) is generally 0.5～20 DEG C/h, preferably 1～ 5℃/h.The time of described constant temperature is more than 0.5 hour, preferably 0.5～10 hour.
In the method for the present invention, the heating rate of step e) is generally 0.5～20 DEG C/h, preferably 1～5 DEG C /h.The time of described constant temperature is more than 0.5 hour, preferably 0.5～10 hour.
Separation described in step f) can use the routine operation of this area, as used decompression distillation Product is separated, purifies by method.The process conditions of decompression distillation procedure are: pressure is 5～20kPa (0.1-0.15atm), preferably 10～15kPa, the heating rate in still-process is generally 0.5～20 DEG C / h, preferably 1～10 DEG C/h.
In step f), distilled by decompression, generally the product of step e) is cut into ＜ 150 DEG C Fraction, 150 DEG C of-275 DEG C of fractions and 275 DEG C of fraction three part distillations of ＞.Three parts after wherein purifying The use of distillation can follow following principle: initial temperature to 150 DEG C part can participate in follow-up as raw material Produce, 150 DEG C of-275 DEG C of fractions are standard ASA product, 275 DEG C of fractions of ＞ to latter end are wanted at product Ask be not extra high in the case of can be doped in Part II use, otherwise need to be waste treatment (＞ 275 DEG C evaporate content and account for about 5wt%).
Compared with prior art, the method for the present invention has a technique effect highlighted below:
1, in the present invention, by increasing by 125～180 DEG C of isothermal reaction sections in course of reaction, can improve Reactant is fully contacted mixing and the degree of effecting reaction, thus effectively reduces the generation of side reaction.
2, target product yield can improve more than 10 percentage points and reaches 65%, significantly reduces simultaneously The side reaction of course of reaction.
3, use coking that strict product purifying technique can effectively prevent product in purification process with Run off, improve purity and the Color Quality of target product.
4, compared with prior art, the method technological process of the present invention is reasonable, effectively reduces side reaction Generation, the purity of product and color and luster have also been obtained and improve significantly.
Detailed description of the invention
Below by specific embodiment, the method for the present invention is described in further detail.
In embodiment, raw material C used13Interior alkene, C14Interior alkene is not less than by commercially available acquisition, purity requirement 85%.Maleic anhydride by commercially available acquisition, purity be chemical pure level and more than.Chromatogram quantification is utilized to divide The area normalization method of analysis calculates product yield.
Selective computational methods are:
Embodiment 1
A) 100g carbon 13 internal olefin and 50g carbon 14 internal olefin are mixed, obtain internal olefin and mix Compound；
B) mixtures of internal olefins of step a) is uniformly mixed according to the mol ratio of 2:1 with maleic anhydride Close；
C) raw material speed with 5 DEG C/h is mixed obtained by step b) from room temperature to 80 DEG C, constant temperature 40min, makes reaction raw materials be completely melt；
D) by step c) gained initial mixture with the ramp of 10 DEG C/h to 160 DEG C, and at this At a temperature of isothermal reaction 30min；
E), after 160 DEG C of constant temperature terminate, continue, with the speed of 5 DEG C/h, reaction temperature is warming up to 200 DEG C, Constant temperature 4h, reaction terminates；
F) step e) gained product subtracts in pressure 10kPa, the condition of 2 DEG C/h of heating rate Pressure distillation, respectively obtains 150 DEG C of fractions of ＜, 150 DEG C of-275 DEG C of fractions and 275 DEG C of fractions of ＞, wherein 150 DEG C of i.e. alkenyl succinic acid anhydride products of-275 DEG C of fractions (chromatography checking).
Wherein, conversion ratio is 80%, and the yield of 150 DEG C of-275 DEG C of fractions is 60wt%, and selectivity is 98%. Transparent clear amber liquid.
Embodiment 2
A) 200g carbon 13 internal olefin and 50g carbon 14 internal olefin are mixed, obtain internal olefin and mix Compound；
B) mixtures of internal olefins of step a) is uniformly mixed according to the mol ratio of 3:1 with maleic anhydride；
C) raw material speed with 5 DEG C/h is mixed obtained by step b) from room temperature to 90 DEG C, constant temperature 30min, makes reaction raw materials be completely melt；
D) by step c) gained initial mixture with the ramp of 10 DEG C/h to 170 DEG C, and at this At a temperature of isothermal reaction 40min；
E), after 160 DEG C of constant temperature terminate, continue, with the speed of 5 DEG C/h, reaction temperature is warming up to 210 DEG C, permanent Temperature 5h, reaction terminates；
F) step e) gained product subtracts in pressure 10kPa, the condition of 5 DEG C/h of heating rate Pressure distillation, respectively obtains 150 DEG C of fractions of ＜, 150 DEG C of-275 DEG C of fractions and 275 DEG C of fractions of ＞, wherein 150 DEG C of i.e. alkenyl succinic acid anhydride products of-275 DEG C of fractions (chromatography checking).
Wherein, conversion ratio is 80.3%, and the yield of 150 DEG C of-275 DEG C of fractions is 60.2wt%, and selectivity is 98.3%, transparent clear amber liquid.
Embodiment 3
A) 240g carbon 13 internal olefin and 40g carbon 14 internal olefin are mixed, obtain internal olefin and mix Compound；
B) mixtures of internal olefins of step a) is uniformly mixed according to the mol ratio of 5:1 with maleic anhydride Close；
C) raw material speed with 5 DEG C/h is mixed obtained by step b) from room temperature to 85 DEG C, constant temperature 40min, makes reaction raw materials be completely melt；
D) by step c) gained initial mixture with the ramp of 10 DEG C/h to 160 DEG C, and at this At a temperature of isothermal reaction 50min；
E), after 160 DEG C of constant temperature terminate, continue, with the speed of 5 DEG C/h, reaction temperature is warming up to 220 DEG C, permanent Temperature 3.5h, reaction terminates；
F) step e) gained product subtracts in pressure 10kPa, the condition of 5 DEG C/h of heating rate Pressure distillation, respectively obtains 150 DEG C of fractions of ＜, 150 DEG C of-275 DEG C of fractions and 275 DEG C of fractions of ＞, wherein 150 DEG C of i.e. alkenyl succinic acid anhydride products of-275 DEG C of fractions (chromatography checking).
Wherein, conversion ratio is 79.8%, and the yield of 150 DEG C of-275 DEG C of fractions is 59.4wt%, and selectivity is 97.1%, transparent clear amber liquid.
Comparative example 1
Using the conventional method of this area, wherein the proportioning of reaction mass is with embodiment 1, including herein below:
A) 100g carbon 13 internal olefin and 50g carbon 14 internal olefin are mixed, obtain internal olefin and mix Compound；
B) mixtures of internal olefins of step a) is uniformly mixed according to the mol ratio of 2:1 with maleic anhydride Close；
C) raw material speed with 5 DEG C/h is mixed obtained by step b) from room temperature to 80 DEG C, constant temperature 40min, makes reaction raw materials be completely melt；
D) continuing, with the speed of 5 DEG C/h, reaction temperature is warming up to 200 DEG C, constant temperature 4h, reaction terminates；
E) separation of product is with embodiment 2.
Wherein the yield of 150 DEG C of-275 DEG C of fractions is 60.2wt%, and selectivity is 98.3%.Transparency is poor, The darkest amber color liquid.
Comparative example 2
Using the conventional method of this area, wherein the proportioning of reaction mass is with embodiment 2, including herein below:
A) 200g carbon 13 internal olefin and 50g carbon 14 internal olefin are mixed, obtain internal olefin and mix Compound；
B) mixtures of internal olefins of step a) is uniformly mixed according to the mol ratio of 3:1 with maleic anhydride Close；
C) raw material speed with 5 DEG C/h is mixed obtained by step b) from room temperature to 80 DEG C, constant temperature 40min, makes reaction raw materials be completely melt；
D) continuing, with the speed of 5 DEG C/h, reaction temperature is warming up to 200 DEG C, constant temperature 4h, reaction terminates；
E) separation of product is with embodiment 1.
Wherein the yield of 150 DEG C of-275 DEG C of fractions is 59.7wt%, and selectivity is 97.5%.Transparency is poor, The darkest amber color liquid.

Claims (10)

1. the method producing alkenyl succinic anhydride, including herein below:
A) carbon 13 internal olefin and carbon 14 internal olefin are mixed to form mixtures of internal olefins, described carbon 13 Internal olefin and carbon 14 internal olefin are the linear internal of carbon number 13～14 respectively, described carbon 13 The mass ratio of internal olefin and carbon 14 internal olefin is 1.5:1～8:1；
B) by the mixtures of internal olefins of step a) and maleic anhydride according to the mol ratio of 1.5:1～8:1 Uniformly mixing；
C) obtained by step b), mixing raw material is warming up to 50～120 DEG C, and constant temperature more than 0.1 hour makes Reaction raw materials is completely melt；
D) by step c) gained initial mixture from room temperature to 125～180 DEG C, and in this temperature Lower isothermal reaction more than 0.1 hour；
E) after 125～180 DEG C of constant temperature terminate, continuing reaction temperature is warming up to 190～230 DEG C, constant temperature is extremely Reaction terminates；
F) step e) gained product is through separating, and obtains alkenyl succinic acid anhydride product.
The most in accordance with the method for claim 1, it is characterised in that the described constant temperature of step c) time Between be 0.1～2 hour；The time of the described constant temperature of step d) is more than 0.5 hour, preferably 0.5～10 Hour；The time of the described constant temperature of step e) is more than 0.5 hour, preferably 0.5～10 hour.
The most in accordance with the method for claim 1, it is characterised in that alkene in carbon 13 in step a) The purity of hydrocarbon and carbon 14 internal olefin is more than 80%, and preferably more than 95%.
The most in accordance with the method for claim 1, it is characterised in that described carbon 13 internal olefin and carbon The mass ratio of 14 internal olefins is 2:1～5:1.
The most in accordance with the method for claim 1, it is characterised in that mixtures of internal olefins and maleic Mol ratio 2:1 of dicarboxylic anhydride～5:1.
The most in accordance with the method for claim 1, it is characterised in that step c), step d) and step Heating rate described in e) is 0.5～20 DEG C/h.
The most in accordance with the method for claim 1, it is characterised in that the separation described in step f) Using distillation under vacuum, the process conditions of the distillation procedure that reduces pressure are: pressure is 5～20kPa, still-process In heating rate be 0.5～20 DEG C/h.
8. according to the method described in claim 1 or 7, it is characterised in that the reaction of step e) is produced Thing cuts out 150 DEG C of fractions of ＜, 150 DEG C of-275 DEG C of fractions and 275 DEG C of fraction three part distillations of ＞.
The most in accordance with the method for claim 8, it is characterised in that described 150 DEG C-275 DEG C evaporate Divide and be standard ASA product.
The most in accordance with the method for claim 8, it is characterised in that 150 DEG C of parts of ＜ are as raw material Participate in producing next time, directly use as mixing raw material；Described ＞ 275 DEG C evaporates and is doped to 150 DEG C-275 DEG C Fraction uses or as garbage.
CN201610220253.9A 2016-04-07 2016-04-07 Method for producing alkenyl succinic anhydride Pending CN105924415A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112961128A (en) * 2021-02-19 2021-06-15 上海昶法新材料有限公司 Novel production process device for preparing ASA
CN113045518A (en) * 2021-02-05 2021-06-29 上海昶法新材料有限公司 Method for continuously preparing alkenyl succinic anhydride by using microchannel reactor
CN113149939A (en) * 2021-02-05 2021-07-23 上海昶法新材料有限公司 Method for preparing alkenyl succinic anhydride by tubular reactor

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113045518A (en) * 2021-02-05 2021-06-29 上海昶法新材料有限公司 Method for continuously preparing alkenyl succinic anhydride by using microchannel reactor
CN113149939A (en) * 2021-02-05 2021-07-23 上海昶法新材料有限公司 Method for preparing alkenyl succinic anhydride by tubular reactor
CN112961128A (en) * 2021-02-19 2021-06-15 上海昶法新材料有限公司 Novel production process device for preparing ASA
CN112961128B (en) * 2021-02-19 2023-05-16 上海昶法新材料有限公司 Novel production process device for preparing ASA

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