CN1393437A - Method for preparing alkenyl succinic anhydride by using carbon tridecane and tetradecene - Google Patents
Method for preparing alkenyl succinic anhydride by using carbon tridecane and tetradecene Download PDFInfo
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- CN1393437A CN1393437A CN 01119909 CN01119909A CN1393437A CN 1393437 A CN1393437 A CN 1393437A CN 01119909 CN01119909 CN 01119909 CN 01119909 A CN01119909 A CN 01119909A CN 1393437 A CN1393437 A CN 1393437A
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- CN
- China
- Prior art keywords
- carbon
- alkene
- alkenyl succinic
- succinic anhydride
- anhydride
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- -1 alkenyl succinic anhydride Chemical compound 0.000 title claims abstract description 29
- 229940014800 succinic anhydride Drugs 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 14
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 title claims description 13
- 229940095068 tetradecene Drugs 0.000 title claims description 9
- KGKBZHYOISCHCV-UHFFFAOYSA-N CCCCCCCCCCCCC.[C] Chemical compound CCCCCCCCCCCCC.[C] KGKBZHYOISCHCV-UHFFFAOYSA-N 0.000 title 1
- 150000001336 alkenes Chemical class 0.000 claims abstract description 55
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 239000012188 paraffin wax Substances 0.000 claims abstract description 4
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 22
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims description 17
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 238000005194 fractionation Methods 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical compound [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 230000002459 sustained effect Effects 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005336 cracking Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical group CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- CTWYWOFTJYYYFX-UHFFFAOYSA-N C=CCCCCCCCCCCCC.[C] Chemical compound C=CCCCCCCCCCCCC.[C] CTWYWOFTJYYYFX-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for preparing alkenyl succinic anhydride by using C13-C14 mixed olefin is characterized in that C11-C14 normal paraffin is used as a raw material, the raw material is dehydrogenated by a Pacol process, and then the C13-C14 mixed olefin is obtained by separating the alkane and the olefin by an OLEX process, wherein the purity of the olefin is 85-93%, the normal structure rate is more than 90%, the carbon number of the raw material olefin is centralized, the purity is high, and the quality is good.
Description
The present invention relates to a kind of Organic Chemicals of papermaking neutral sizing, promptly utilize carbon 13, tetradecene hydrocarbon to produce the method for alkenyl succinic anhydride.
Alkenyl succinic anhydride is widely used in a kind of fine-chemical intermediate of light industry by developed country, its preparation is sizing agent, the water-resisting agent of excellent property in papermaking, be the water-resisting agent of leather textiles simultaneously, its derivative has wideer range of application.Neutral sizing agent is the additive that developed country's paper-making industry adopts already, and it has increased substantially the quality of paper, however China prolong with ancient glue applying method always, cause the quality product of paper lower.The main technique route of the synthetic alkenyl succinic anhydride of developed country is at present:
Wax cracking → alhpa olefin → isomerization → internal olefin → synthetic
Vinyl polymerization → alhpa olefin → isomerization → internal olefin → synthetic
The preceding kind product carbon number range that technology obtained is wide, has high carbene synthetics, rerum natura refractive index height, and viscosity is bigger, be fit to papermaking and use, but because material purity is lower, synthetic yield is lower, the positive structure rate of raw material alkene is lower, and it is also low to cause product effectively to be formed, and this is the problem place of this technology.Thereby the high effect that influences of alhpa olefin content in the handicraft product is planted in the back.
The object of the present invention is to provide a kind of raw material olefin carbon number to concentrate purity height, the measured method of utilizing carbon 13, tetradecene hydrocarbon to produce alkenyl succinic anhydride of matter.
The present invention is achieved in that with carbon 13～14 mixed olefins, generate alkenyl succinic anhydride with the MALEIC ANHYDRIDE hybrid reaction, normal paraffin with carbon 11～14 is a raw material, through the dehydrogenation of Pacol technology, separate the carbon 13～14 that obtains through OLEX technology alkane alkene again and mix alkene, alkene purity reaches 85～93%, and positive structure rate reaches more than 90%, and wherein interior alkene content is more than 80%; React alkene (mol) in synthesis reactor with MALEIC ANHYDRIDE: cis-butenedioic anhydride (mol)=1: 0.7～0.9, temperature of reaction are 180～230 ℃, and the reaction times is 16～22 hours, obtain the alkenyl succinic anhydride crude product, obtain pure products behind vacuum fractionation.
Resulting crude product is that fractionated light fraction can directly turn back in carbon 13～14 total hydrocarbon feeds, also can directly carry out building-up reactions as mixed olefin feedstock and MALEIC ANHYDRIDE.
A kind of intermediates are arranged, i.e. carbon 13, tetradecene, purity is near 90%, and positive structure rate reaching more than 90%, is the synthetic alkenyl succinic anhydride of raw material with this alkene, the product purity height, carbon number is concentrated, the effective ingredient height, and also technological process is simple, and condition relaxes.Also open up new way simultaneously for the application of washing factory carbon 13, tetradecene, in the production process of synthetic fatty alcohol, because carbon 13, tetradecene have surpassed the ratio that requires in the raw material, this part therefore superfluous precious alkene just becomes and improves the important topic that product is formed.
Technological process of the present invention is simple.The used alkene of the present invention is the intermediates of synthetic fatty alcohol, need not through processing again, and prior art then is that raw material olefin needs to produce internal olefin through the isoversion reaction after alhpa olefin is produced in wax cracking.
The raw material olefin carbon number is concentrated, the purity height, and quality is good.Through an alkene carbon containing 13～14 alkene of PACOLl, OLEX explained hereafter, purity reaches 85～93%, and positive structure rate is up to more than 90%, and interior alkene is more than 80%, and the raw material olefin carbon number of prior art is wide, and isomery alkene is many, α alkene oils content height.Contain 15～20% unconverted oil in the wax cracking alkene, positive structure rate 60～80% in the alkene, carbon number can reach 8～10.
Product structure is simple, and purity height, the alkenyl succinic anhydride of being produced are essentially carbon 13～14 acid anhydrides, and the purity height is beneficial to the derived product raw materials for production.And the product structure complexity of prior art, productive rate is low, and the interior alkene content of straight chain is lower in the olefin feedstock, and carbon number is wide, and the alkenyl succinic anhydride complex structure of being produced is unfavorable for producing the high purity fine chemical product as middle deep processing.
Utilize the laboratory facilities of orthogonal design, two kinds of proportion of raw materials to synthetic alkenyl succinic anhydride, and the temperature of reaction when synthetic, reaction times and additive are selected and are investigated, and have obtained to be fit to mix with carbon 13,14 optimum process condition of the synthetic alkenyl succinic anhydride of alkene.
(1) normal paraffin with carbon 11～14 is that raw material separates carbon 13～14 mixing alkene that generate through OLEX technology alkane alkene again through the dehydrogenation of PACOL technology, and alkene purity reaches 85～93%, and positive structure rate reaches more than 90%, and wherein interior alkene content is more than 80%.
(2) be that raw material reacts in synthesis reactor with above-mentioned mixed olefins and MALEIC ANHYDRIDE, alkene (mol): cis-butenedioic anhydride (mol)=1: 0.7～0.9.
Temperature of reaction is 180～230 ℃ in (3) (2).
The reaction times is 16～22 hours in (4) (2).
Synthetics cuts out unreacting material and product through vacuum fractionation in (5) (2), 200～250 ℃ of cutting cuts.
The unreacting material that cuts out in (6) (5) mixes raw material olefin as reaction raw materials again.
Embodiment:
Example 1,380.2 gram carbon 13～14 are mixed alkene (wherein carbon containing 13 alkene 37.8%, carbon 14 alkene 51.6%) and 156.9 gram MALEIC ANHYDRIDE thorough mixing in an airtight triangular flask, are heated to about 205 ℃, continue 18 hours, the thick product of 495 grams.Thick product is collected product 189 grams after underpressure distillation.
Example 2, alkene carbon containing tridecylene 37.8%, carbon tetradecene 51.6%, MALEIC ANHYDRIDE purity 99.0%.
In the 100l enamel reaction still, mix stirring with above-mentioned alkene 52.88Kg and MALEIC ANHYDRIDE 20.68Kg and be warming up to 230 ℃, sustained reaction 20 hours, thick product is collected 200～250 ℃ of cut meter 40.7Kg under vacuum fractionation.
Example 3, with example 2 component same materials: alkene 58.82Kg, MALEIC ANHYDRIDE 16.00Kg mix to stir in example 2 reactors and are warming up to 220 ℃, sustained reaction 20 hours, thick product is collected 200～250 ℃ of cut meter 37.6Kg under vacuum fractionation.
Example 4, with example 2 component same materials: alkene 58.82Kg, MALEIC ANHYDRIDE 16.70Kg are warming up to 190 ℃ mixing to stir in example 2 reactors, sustained reaction 18 hours, thick product is collected 200～250 ℃ of cut meter 39.5Kg under vacuum fractionation.
Example 5, with example 2 component same materials: alkene 54.00Kg, MALEIC ANHYDRIDE 14.77Kg are warming up to 205 ℃ mixing to stir in example 2 reactors, sustained reaction 18 hours, thick product is collected 200～250 ℃ of cut meter 34.3Kg under vacuum fractionation.
Example 6, mix to stir with fractionated lighting end in the example 5 thick products (wherein carbon tridecylene hydrocarbon is 32.2%, carbon tetradecene hydrocarbon is 50.3%) the 54.68Kg MALEIC ANHYDRIDE 11.00Kg identical that be raw material and be warming up to 205 ℃ with example 2, sustained reaction 17 hours, thick product is collected 200～250 ℃ of cut meter 26.3Kg under vacuum fractionation.
Claims (2)
1. utilize carbon 13, tetradecene hydrocarbon to produce the method for alkenyl succinic anhydride, it is characterized in that: with carbon 13～14 mixed olefins, generate alkenyl succinic anhydride with the MALEIC ANHYDRIDE hybrid reaction, normal paraffin with carbon 11～14 is a raw material, through the dehydrogenation of Pacol technology, to separate the carbon 13～14 that obtains through OLEX technology alkane alkene again and mix alkene, alkene purity reaches 85～93%, positive structure rate reaches more than 90%, and wherein interior alkene content is more than 80%; React alkene (mol) in synthesis reactor with MALEIC ANHYDRIDE: cis-butenedioic anhydride (mol)=1: 0.7～0.9, temperature of reaction are 180～230 ℃, and the reaction times is 16～22 hours, obtain the alkenyl succinic anhydride crude product, obtain pure products behind vacuum fractionation.
2. the method for utilizing carbon 13, tetradecene hydrocarbon to produce alkenyl succinic anhydride according to claim 1, it is characterized in that: resulting crude product, be that fractionated light fraction can directly turn back in carbon 13～14 total hydrocarbon feeds, also can directly carry out building-up reactions as mixed olefin feedstock and MALEIC ANHYDRIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01119909 CN1393437A (en) | 2001-06-29 | 2001-06-29 | Method for preparing alkenyl succinic anhydride by using carbon tridecane and tetradecene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01119909 CN1393437A (en) | 2001-06-29 | 2001-06-29 | Method for preparing alkenyl succinic anhydride by using carbon tridecane and tetradecene |
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|---|---|
| CN1393437A true CN1393437A (en) | 2003-01-29 |
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| CN 01119909 Pending CN1393437A (en) | 2001-06-29 | 2001-06-29 | Method for preparing alkenyl succinic anhydride by using carbon tridecane and tetradecene |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496948A (en) * | 2014-12-22 | 2015-04-08 | 苏州天马精细化学品股份有限公司 | Preparation method of alkenyl succinic anhydride |
| CN105924415A (en) * | 2016-04-07 | 2016-09-07 | 辽宁石油化工大学 | Method for producing alkenyl succinic anhydride |
| 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 |
-
2001
- 2001-06-29 CN CN 01119909 patent/CN1393437A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104496948A (en) * | 2014-12-22 | 2015-04-08 | 苏州天马精细化学品股份有限公司 | Preparation method of alkenyl succinic anhydride |
| CN104496948B (en) * | 2014-12-22 | 2017-04-19 | 苏州天马精细化学品股份有限公司 | Preparation method of alkenyl succinic anhydride |
| CN105924415A (en) * | 2016-04-07 | 2016-09-07 | 辽宁石油化工大学 | Method for producing alkenyl succinic anhydride |
| 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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