CN104860905A - Methyl decyl lactone synthetic perfume normal pressure production method - Google Patents
Methyl decyl lactone synthetic perfume normal pressure production method Download PDFInfo
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- CN104860905A CN104860905A CN201510197658.0A CN201510197658A CN104860905A CN 104860905 A CN104860905 A CN 104860905A CN 201510197658 A CN201510197658 A CN 201510197658A CN 104860905 A CN104860905 A CN 104860905A
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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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Abstract
The present invention provides a methyl decyl lactone synthetic perfume normal pressure production method, raw materials are easy to obtain, product yield is high, process conditions are mild, production cost is low, the process of production is free of environmental pollution, and the raw materials cause no production equipment corrosion. The method includes the following steps: a) stirring and mixing evenly acrylic acid, sec-octyl alcohol, initiator di-tertiary butyl peroxide and catalyst boric acid; b) adding the sec-octyl alcohol into a reaction kettle according to the dosage; c) dropwise adding the mixture obtained by the step a) into the reaction kettle for atmospheric pressure reaction; d) stirring at 100-200 DEG C for reaction for 2-5 hours; e) transferring reaction products into a water washing pot, adding clear water for layering, and separating the lower layer water phase; f) transferring upper layer organic phase reaction products to a kettle type distillation tower, heating, recycling the sec-octyl alcohol under vacuum; and g) transferring surplus reaction products into a kettle type rectification tower for fractionation to obtain methyl decyl lactone with the content of 99%.
Description
Technical field
The present invention relates to fine chemistry industry production technical field, be specifically related to a kind of production method of methyl decalactone synthetic perfume.
Background technology
Methyl decalactone chemical name is 5-methyl-5-hexyl-2 (3H) furanone, and CAS numbers
7011-83-8,have another name called γ methyl-decalactone, dihydro jasmine lactone, γ-methyl-γ-decalactone, there is the fragrance of a flower fragrance of cape jasmine style, and with the fragrant note of fruital, coconut fragrance and green grass or young crops.Methyl decalactone outward appearance is colourless to weak yellow liquid, boiling point 160 ° of C/18mmHg, flash-point > 110 DEG C, relative density 0.930 ~ 0.950(25/25 DEG C), refractive index 1.440 ~ 1.460(20 DEG C).In daily chemical essence, be widely used in all kinds of jasmin, fruital odor type, have good fixation effect.
Methyl decalactone also can be used as foodstuff additive, GRAS is regarded as by FEMA, FEMA numbering 3786, and edible through food and drug administration (FDA) approval, also list the food spice that China's " foodstuff additive use hygienic standard (GB2760-2011) " regulation allows to use in simultaneously.FEMA uses limitation for (mg/kg): frozen milk prod, milk-product, fruit Ice, 0.5 ~ 1.0; Soft sweets, hard candy, 0.5 ~ 1.5; Baked goods, gel product, pudding, nonalcoholic bevarage, 1.0 ~ 3.0; Chewy gum 1.0 ~ 2.0; Containing alcoholic beverage 1.0 ~ 5.0.In food flavor(ing), apply its fruital, the fragrance of a flower, peach, coconut fragrance, also can widely apply with in, Feed Flavourings at cigarette simultaneously.
The dominating process route of methyl decalactone synthesis comprises:
(1) intramolecular reaction is directly synthesized: utilize intramolecular reaction alcohol acid, hydroxy ester and hydroxy-acid derivative can be converted into lactone.Catalyzer generally adopts mineral acid (example hydrochloric acid, sulfuric acid etc.), organic acid (as tosic acid).Because raw material is difficult to obtain, and produce a large amount of acid waste water, the utilization that method is converted into lactone thus has certain limitation.
(2) substituted epoxy ethane and malonic ester condensation method: alkyl epoxy ethane and sodium are for diethyl malonate condensation, and decarboxylation generates gamma lactone.This method technique is simple, and yield is higher.But raw materials used 1,2-oxyethane is difficult to produce, and therefore applies and is restricted.
(3) Reformatsky reaction synthesis method: carbonyl compound (enanthaldehyde) and β-halogen ester (Beta-bromo propionic ester) are carried out condensation in the presence of zinc, obtain beta-hydroxy acid esters, then under acid catalysis, dehydration generates corresponding gamma lactone.China's Viscotrol C aboundresources, cracking Viscotrol C obtains a large amount of enanthaldehyde.This method employs natural matter enanthaldehyde as raw material, has certain development prospect, but has used organic zinc reagent in building-up process, and must react in inert solvent, also must be for further study for realizing industrialization.
Summary of the invention
Technical problem to be solved by this invention is the normal-pressure production method providing a kind of methyl decalactone synthetic perfume, and its raw material is easy to get, and product yield is high, processing condition are gentle, production cost is lower, and non-environmental-pollution in production process, raw material is corrosion-free to production unit.
For solving the problems of the technologies described above, the production method of methyl decalactone synthetic perfume of the present invention, comprises the following steps:
A) first vinylformic acid, sec-octyl alcohol, two-tert-butyl peroxide as initiator, the boric acid as catalyzer are put in agitator kettle, be uniformly mixed, control batch temperature-20 ~ 30 DEG C; In this step, the dosage of sec-octyl alcohol and acrylic acid mol ratio are 1: 1 ~ 10: 1; The dosage of two-tert-butyl peroxide and acrylic acid mol ratio are 0.05: 1 ~ 1: 1; The dosage of boric acid is 0. 5% ~ 5% of vinylformic acid weight;
B) sec-octyl alcohol is metered in reactor by header tank, reactor is warming up to 100 DEG C ~ 200 DEG C; In this step, the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 1: 1 ~ 20: 1;
C) be added drop-wise in the reactor of b) step by a) step gained ingredients mixture by dripping pump, controlling temperature of reaction during dropping is 100 DEG C ~ 200 DEG C, and reaction pressure is normal pressure, time for adding 5 ~ 20 hours;
D) after dropping terminates, continue to keep temperature of reaction 100 DEG C ~ 200 DEG C stirrings, continue reaction after 2 ~ 5 hours, cooling termination reaction;
E) by the mode of the material returned at the bottom of still, d) step reactor reaction product is transferred in water washing pan, clear water is added by 5 ~ 50% of primitive reaction thing gross weight, stir after 2 hours, stratification, separated by lower floor's aqueous phase by observing visor, the water layer separated proceeds to temporary storage tank and applies mechanically as during lower batch of washing;
F) by the mode of the material returned at the bottom of still, the reaction product of upper organic phase in e) step water washing pan is transferred in still distillation tower, heat up, open vacuum pump, under vacuum pressure 1333 ~ 6667Pa, tower top temperature 90 ~ 180 DEG C of conditions, reclaim the sec-octyl alcohol of surplus;
G) by the mode of the material returned at the bottom of still by residue reaction product in f) step still distillation tower, transfer in autoclave rectifying tower, heat up, open vacuum pump, under vacuum pressure 133 ~ 1000Pa, tower top temperature 90 ~ 180 DEG C, reflux ratio 1: 1 ~ 1: 12 condition, carry out fractionation, obtain the methyl decalactone of content 99%.
Preferably, in described step a), the dosage of sec-octyl alcohol and acrylic acid mol ratio are 1:1 ~ 3:1.
Preferably, in described step a), the dosage of two-tert-butyl peroxide and acrylic acid mole are 0.05:1 ~ 0.5: 1.
Preferably, in described step b), the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 3:1 ~ 8:1.
Preferably, in described step a) and step b), total charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 3:1 ~ 10:1.
Above-mentioned optimal technical scheme provides a best proportioning raw materials, contributes to improving conversion rate of reaction product.
Preferably, in described step a), batch temperature controls at 20 ~ 25 DEG C.
In described step b), reactor material is stainless steel or enamel.
Preferably, in described step c), observe according to visor, water reaction generated in reactor and the trimethyl carbinol separate in time, to reduce production cost, carry high product yield.
Preferably, in described step f), the tower top temperature of still distillation tower controls at 90 ~ 100 DEG C; In described step g), the tower top temperature of autoclave rectifying tower controls at 95 ~ 100 DEG C.Pass through f), the working in coordination of the processing condition such as pressure, temperature of g) two steps, contribute to carrying high product yield further.
Preferably, in described step f), in still distillation tower, fill cy500 stainless steel ripple packing; In described step g), in autoclave rectifying tower, fill cy700 stainless steel ripple packing.
Advantage applies of the present invention exists:
1, in methyl decalactone synthetic perfume production process, use sec-octyl alcohol to carry out Radical Addition in the presence of a free-radical initiator with vinylformic acid and produce methyl decalactone.With industrial chemicals vinylformic acid cheap and easy to get for Material synthesis methyl decalactone, cost is lower, is more satisfactory a kind of industrial process.
2, there is airtight safety in production, simple to operate, main technological steps normal pressure is produced, reaction conditions is gentle, reaction conversion ratio is high, technics comparing is easily implemented, produce the few advantage of three wastes discharge amount in production process, product yield is greatly improved, and product fruital fragrance is pure, fine and smooth, soft.
3, the problem of the environmental pollution of prior art existence, the restriction of equipment corrosion raw material is solved.
Product checking GC condition is: chromatographic column HP-5(30m x 0.32mm x 0.25um); Detector FID, temperature 250 DEG C; Sample introduction: sample size is about 0.2ul, splitting ratio 1:100, injector temperature 250 DEG C; Carrier gas: N2, flow velocity 20L/min, pressure 34.47kPa before post; Chromatograph oven temperature: linear temperature program is from 120 DEG C ~ 190 DEG C, and speed is 5 DEG C/min; Then from 190 DEG C ~ 250 DEG C, speed is 10 DEG C/min, retains 10min.
Embodiment
Embodiment 1
A) vinylformic acid 100kg, sec-octyl alcohol 270kg, initiator two-tert-butyl peroxide 15kg, catalyzer boric acid 2kg are put in 630L agitator kettle, be uniformly mixed, control batch temperature 20 ~ 25 DEG C.
In this step, the dosage of sec-octyl alcohol and acrylic acid mol ratio are 1.49:1; The dosage of two-tert-butyl peroxide and acrylic acid mol ratio are 0.07:1; The dosage of boric acid is 2% of vinylformic acid weight.
B) sec-octyl alcohol 550kg is metered in enamel reaction still by header tank, reactor is warming up to 155 DEG C ~ 160 DEG C.In this step, the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 3.04:1.
Step a), b) in, total charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 4.53:1.
C) be added drop-wise in the reactor of b) step by the ingredients mixture of a) step by dripping pump, controlling temperature of reaction during dropping is 155 DEG C ~ 160 DEG C, and reaction pressure is normal pressure, time for adding 10 ~ 15 hours.
In this step, should by observing visor, water reaction generated in reactor and the trimethyl carbinol separate in time.The trimethyl carbinol is decomposed by initiator two-tert-butyl peroxide produced, and the trimethyl carbinol and water can produce the pure trimethyl carbinol by follow-up molecular sieve dehydration separating treatment, for the production of ditertiary butyl peroxide.
D) after dropping terminates, continue to keep temperature of reaction 155 DEG C ~ 160 DEG C stirrings, continue reaction after 2 hours, cooling termination reaction.
E) by the mode of the material returned at the bottom of still by d) step reactor reaction product, transfer in water washing pan, add the clear water of 250kg, stir after 2 ~ 5 hours, stratification, separated by lower floor's aqueous phase by observing visor, the water layer separated proceeds to temporary storage tank and applies mechanically as during lower batch of washing.In this step, clear water add-on is 26.7% of primitive reaction thing gross weight.
F) by the mode of the material returned at the bottom of the still reaction product by upper organic phase in e) step water washing pan, transfer in still distillation tower, heat up, open vacuum pump, at vacuum pressure 1333 ~ 6667Pa, under tower top temperature 90 ~ 100 DEG C of conditions, reclaim the sec-octyl alcohol of surplus.
G) by the mode of the material returned at the bottom of still by residue reaction product in f) step still distillation tower, transfer in autoclave rectifying tower, heat up, open vacuum pump, at vacuum pressure 133 ~ 1000Pa, under tower top temperature 95 ~ 100 DEG C, reflux ratio 1: 5 ~ 1: 12 condition, carry out fractionation, until tower top temperature declines or zero discharge, cooling stops distillation, and receive bottoms rectification residue, fraction products is the methyl decalactone finished product that content reaches 99%.
Made product is colourless transparent liquid, has fragrance of a flower fragrance, and with fruital note, is 99.35% through gas chromatographic analysis product purity, and detecting refractive index (20 DEG C) is 1.4512, and relative density (25 DEG C) is 0.9386.
Embodiment 2
A) vinylformic acid 400kg, sec-octyl alcohol 1590kg, initiator two-tert-butyl peroxide 80kg, catalyzer boric acid 16kg are put in agitator kettle, be uniformly mixed, control batch temperature 20 ~ 25 DEG C.
In this step, the dosage of sec-octyl alcohol and acrylic acid mol ratio are 2.2:1; The dosage of two-tert-butyl peroxide and acrylic acid mol ratio are 0.2:1; The dosage of boric acid is 4% of vinylformic acid weight.
B) sec-octyl alcohol 3976kg is metered in stainless steel cauldron by header tank, reactor is warming up to 160 DEG C ~ 165 DEG C.In this step, the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 5.5:1.
Step a), b) in, total charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 7.7:1.
C) be added drop-wise in the reactor of b) step by the ingredients mixture of a) step by dripping pump, controlling temperature of reaction during dropping is 160 DEG C ~ 165 DEG C, and reaction pressure is normal pressure, time for adding 15 ~ 20 hours.
In this step, should by observing visor, water reaction generated in reactor and the trimethyl carbinol separate in time.
D) after dropping terminates, continue to keep temperature of reaction 160 DEG C ~ 165 DEG C stirrings, continue reaction after 5 hours, cooling termination reaction.
E) by the mode of the material returned at the bottom of still by d) step reactor reaction product, transfer in water washing pan, add the clear water of 800kg, stir after 5 hours, stratification, separated by lower floor's aqueous phase by observing visor, the water layer separated proceeds to temporary storage tank and applies mechanically as during lower batch of washing.In this step, clear water add-on is 13.2% of primitive reaction thing gross weight.
F) by the mode of the material returned at the bottom of the still reaction product by upper organic phase in e) step water washing pan, transfer in still distillation tower, heat up, open vacuum pump, at vacuum pressure 1333 ~ 6667Pa, under tower top temperature 90 ~ 100 DEG C of conditions, reclaim the sec-octyl alcohol of surplus.
G) by the mode of the material returned at the bottom of still by residue reaction product in f) step still distillation tower, transfer in autoclave rectifying tower, heat up, open vacuum pump, at vacuum pressure 133 ~ 1000Pa, under tower top temperature 95 ~ 100 DEG C, reflux ratio 1: 5 ~ 1: 12 condition, carry out fractionation, until tower top temperature declines or zero discharge, cooling stops distillation, and receive bottoms rectification residue, fraction products is the methyl decalactone finished product that content reaches 99%.
Made product is colourless transparent liquid, has fragrance of a flower fragrance, and with fruital note, is 99.22% through gas chromatographic analysis product purity, and detecting refractive index (20 DEG C) is 1.4519, and relative density (25 DEG C) is 0.9391.
Claims (9)
1. a production method for methyl decalactone synthetic perfume, comprises the following steps:
A) first vinylformic acid, sec-octyl alcohol, two-tert-butyl peroxide, boric acid are put in agitator kettle, be uniformly mixed, control batch temperature-20 ~ 30 DEG C; In this step, the dosage of sec-octyl alcohol and acrylic acid mol ratio are 1: 1 ~ 10: 1; The dosage of two-tert-butyl peroxide and acrylic acid mol ratio are 0.05: 1 ~ 1: 1; The dosage of boric acid is 0. 5% ~ 5% of vinylformic acid weight;
B) sec-octyl alcohol is metered in reactor by header tank, reactor is warming up to 100 DEG C ~ 200 DEG C; In this step, the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 1: 1 ~ 20: 1;
C) be added drop-wise in the reactor of b) step by a) step gained ingredients mixture by dripping pump, controlling temperature of reaction during dropping is 100 DEG C ~ 200 DEG C, and reaction pressure is normal pressure, time for adding 5 ~ 20 hours;
D) after dropping terminates, continue to keep temperature of reaction 100 DEG C ~ 200 DEG C stirrings, continue reaction after 2 ~ 5 hours, cooling termination reaction;
E) by the mode of the material returned at the bottom of still, d) step reactor reaction product is transferred in water washing pan, adding clear water by 5 ~ 50% of primitive reaction thing gross weight, stir after 2 hours, stratification, by observing visor, lower floor's aqueous phase being separated;
F) by the mode of the material returned at the bottom of still, the reaction product of upper organic phase in e) step water washing pan is transferred in still distillation tower, heat up, open vacuum pump, under vacuum pressure 1333 ~ 6667Pa, tower top temperature 90 ~ 180 DEG C of conditions, reclaim the sec-octyl alcohol of surplus;
G) by the mode of the material returned at the bottom of still by residue reaction product in f) step still distillation tower, transfer in autoclave rectifying tower, heat up, open vacuum pump, under vacuum pressure 133 ~ 1000Pa, tower top temperature 90 ~ 180 DEG C, reflux ratio 1: 1 ~ 1: 12 condition, carry out fractionation, obtain the methyl decalactone of content 99%.
2. the production method of methyl decalactone synthetic perfume as claimed in claim 1, it is characterized in that: in described step a), the dosage of sec-octyl alcohol and acrylic acid mol ratio are 1:1 ~ 3:1.
3. the production method of methyl decalactone synthetic perfume as claimed in claim 1, is characterized in that: in described step a), and the dosage of two-tert-butyl peroxide and acrylic acid mole are 0.05:1 ~ 0.5: 1.
4. the production method of methyl decalactone synthetic perfume as claimed in claim 1, it is characterized in that: in described step b), the charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 3:1 ~ 8:1.
5. the production method of methyl decalactone synthetic perfume as claimed in claim 1, is characterized in that: in described step a) and step b), total charging capacity of sec-octyl alcohol and acrylic acid mol ratio are 3:1 ~ 10:1.
6. the production method of transesterify synthesizing methyl decalactone as claimed in claim 1, it is characterized in that: in described step a), batch temperature controls at 20 ~ 25 DEG C.
7. the production method of methyl decalactone synthetic perfume as claimed in claim 1, is characterized in that: in described step c), and water reaction generated in reactor and the trimethyl carbinol separate.
8. the production method of methyl decalactone synthetic perfume as claimed in claim 1, it is characterized in that: in described step f), the tower top temperature of still distillation tower controls at 90 ~ 100 DEG C; In described step g), the tower top temperature of autoclave rectifying tower controls at 95 ~ 100 DEG C.
9. the production method of methyl decalactone synthetic perfume as claimed in claim 1, is characterized in that: in described step f), fills cy500 stainless steel ripple packing in still distillation tower; In described step g), in autoclave rectifying tower, fill cy700 stainless steel ripple packing.
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| CN201510197658.0A CN104860905A (en) | 2015-04-24 | 2015-04-24 | Methyl decyl lactone synthetic perfume normal pressure production method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997269A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of method of reactive distillation synthesis arbricolin synthetic perfume |
| CN108997270A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of production method of reactive distillation synthesis gamma decalactone synthetic perfume |
-
2015
- 2015-04-24 CN CN201510197658.0A patent/CN104860905A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 宣慧: "γ-内酯的合成", 《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997269A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of method of reactive distillation synthesis arbricolin synthetic perfume |
| CN108997270A (en) * | 2018-08-06 | 2018-12-14 | 安徽华业香料股份有限公司 | A kind of production method of reactive distillation synthesis gamma decalactone synthetic perfume |
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