WO2021104082A1 - 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用 - Google Patents

利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用 Download PDF

Info

Publication number
WO2021104082A1
WO2021104082A1 PCT/CN2020/129090 CN2020129090W WO2021104082A1 WO 2021104082 A1 WO2021104082 A1 WO 2021104082A1 CN 2020129090 W CN2020129090 W CN 2020129090W WO 2021104082 A1 WO2021104082 A1 WO 2021104082A1
Authority
WO
WIPO (PCT)
Prior art keywords
cigarette
extract
extraction
tar
molecular distillation
Prior art date
Application number
PCT/CN2020/129090
Other languages
English (en)
French (fr)
Inventor
李力群
纪旭东
柴颖
张峻松
陈晨
郭春生
叶亚军
田数
王旭东
乔月梅
李瑞丽
梁淼
张文洁
Original Assignee
内蒙古昆明卷烟有限责任公司
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 内蒙古昆明卷烟有限责任公司 filed Critical 内蒙古昆明卷烟有限责任公司
Priority to EP20891974.6A priority Critical patent/EP4059358B1/en
Priority to US17/780,543 priority patent/US11839232B2/en
Priority to JP2022531435A priority patent/JP7340104B2/ja
Priority to KR1020227021024A priority patent/KR102614469B1/ko
Publication of WO2021104082A1 publication Critical patent/WO2021104082A1/zh

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/12—Chemical features of tobacco products or tobacco substitutes of reconstituted tobacco
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B3/00—Preparing tobacco in the factory
    • A24B3/12—Steaming, curing, or flavouring tobacco
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02—Manufacture of tobacco smoke filters
    • A24D3/0204—Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212—Applying additives to filter materials
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/04—Tobacco smoke filters characterised by their shape or structure
    • A24D3/048—Tobacco smoke filters characterised by their shape or structure containing additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/10—Vacuum distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/12—Molecular distillation
    • 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
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the invention relates to a method for preparing a tar extract with aroma-generating properties by using waste cigarette butts and its application in cigarettes, and belongs to the technical field of tobacco technology.
  • Cigarette butts are by-products after cigarette consumption, mainly composed of filter rods, residual shredded tobacco, cigarette paper, tipping paper, etc. my country is a big country in the production and consumption of cigarettes. With the large number of cigarettes consumed every year, many discarded cigarette butts are produced, which are discarded and pollute the environment.
  • the tar substances trapped in the discarded cigarette butts contain not only ketones, furans, pyrazines and other aroma components that have a positive effect on sensory quality, but also nicotine that can enhance consumers' physiological satisfaction, as well as amines and aldehydes. Such as harmful substances that have obvious negative effects on the senses. Therefore, it is of great significance to extract tar substances in waste cigarette butts and prepare extracts with certain properties or functions.
  • Subcritical extraction technology is another new type of extraction and separation technology developed after supercritical. It uses subcritical fluid as the extraction solvent to extract under airtight, oxygen-free, low-pressure, and low-temperature conditions.
  • the solvent is easy to recover and has no residue, and it is difficult to extract products.
  • the advantages of oxidation, wide selection of solvents, low extraction pressure and low requirements for reaction equipment have attracted increasing attention and have been popularized and applied.
  • CN109959649A discloses a cigarette tar extract with chemiluminescence properties.
  • the preparation method of the cigarette tar extract includes the following steps: adding the cigarette tar into a reagent for extraction to obtain the cigarette tar extract.
  • the cigarette tar can be prepared by the following steps: smoking cigarettes, filtering the generated smoke, and collecting smoke particles to obtain cigarette tar.
  • the cigarette tar extract in the patent is prepared by ultrasonic extraction in an open system under natural light conditions. Therefore, the luminescent substance contained is stable in nature and is not sensitive to factors such as light, oxygen and temperature; the extract is sensitive to the pH of the medium. The luminescence response range is wide, and chemiluminescence reactions can occur under acidic, neutral or alkaline conditions.
  • the cigarette tar in the patent is the tar in the smoke particulate phase, and the prepared tar extract has luminous properties, and does not involve the extraction of the tar in the cigarette butt to obtain the tar aroma component.
  • CN102559388A discloses a tobacco essential oil and its preparation method and application in cigarettes, wherein the tobacco essential oil is prepared by the following method: waste tobacco powder ⁇ organic solvent extraction ⁇ crude oil extract ⁇ water vapor ⁇ condensation ⁇ oil-water separation ⁇ Tobacco essential oil. Adding the tobacco essential oil of the present invention as a flavoring agent to cigarette shreds can increase the original tobacco flavor, improve the quality of the cigarette flavor, reduce tobacco irritation and miscellaneous fumes, and soften the smoke.
  • the patent uses the waste tobacco dust produced in the production process of cigarettes as raw materials, and the waste tobacco dust does not contain tar components, and does not involve the extraction process of the cigarette butts.
  • the purpose of the present invention is to provide a method for preparing a tar extract with aromatizing properties by using waste cigarette butts.
  • the invention uses waste cigarette butts as raw materials, adopts subcritical extraction and molecular distillation separation to obtain a tar extract with aroma-making properties, and applies the obtained tar extract to cigarettes, which can improve the aroma of the cigarettes.
  • the raw material discarded cigarette butts used in the present invention are cigarette butts discarded in ashtrays, roadsides, etc. after people consume cigarettes.
  • the raw material sources are wide and the cost is low; the color of the discarded cigarette butts used is yellow; the color of the present invention is yellow.
  • Cigarette butts contain higher tar content.
  • the present invention provides a method for preparing a tar extract with aromatizing properties by using waste cigarette butts, the method comprising the following steps:
  • the extraction solvent is at least one of n-butane, ethanol, petroleum ether, n-hexane, acetone, dichloromethane, and ethyl acetate;
  • the ratio of waste cigarette butts to extraction solvent is 1 g: 5 to 80 mL.
  • the conditions of the subcritical extraction are: extraction pressure 0.6-1.6 MPa, extraction temperature 20-60°C, extraction time 10-120 min, and extraction times 1-3 times. More preferably, the extraction pressure is 0.7 to 1.2 MPa, and the lower limit of the extraction pressure is selected from 0.8 MPa, 0.9 MPa, 1.0 MPa or 1.1 MPa. The upper limit of the extraction pressure is selected from 0.8 MPa, 0.9 MPa, 1.0 MPa or 1.1 MPa. More preferably, the extraction temperature is 30-50°C, the lower limit of the extraction temperature is selected from 35°C, 40°C, or 45°C, and the upper limit of the extraction temperature is selected from 35°C, 40°C, or 45°C. More preferably, the extraction time is 50-100min, the lower limit of the extraction time is selected from 60min, 70min, 80min or 90min, and the upper limit of the extraction time is selected from 60min, 70min, 80min or 90min.
  • the temperature of the vacuum distillation is 25 to 45° C.
  • the pressure is 0.06 to 0.08 Mpa.
  • the molecular distillation is a two-stage molecular distillation, combining the light components of one-stage and two-stage molecular distillation;
  • the heating temperature of the first-stage molecular distillation is 50-80°C
  • the pressure is 100-200Pa
  • the feed rate is 300-600mL/h
  • the scraping speed is 200-300rpm; more preferably, the heating of the first-stage molecular distillation
  • the temperature is 60 ⁇ 70°C. More preferably, the pressure is 110Pa ⁇ 190Pa; the lower limit of the pressure is selected from 120Pa, 130Pa, 140Pa, 150Pa, 160Pa, 170Pa or 180Pa, and the upper limit of the pressure is selected from 120Pa, 130Pa, 140Pa, 150Pa, 160Pa, 170Pa or 180Pa.
  • the heating temperature of the two-stage molecular distillation is 90-110°C, the pressure is 40-60 Pa, the feeding speed is 300-600 mL/h, and the film scraping speed is 200-300 rpm. More preferably, the heating temperature of the two-stage molecular distillation is 95-105° C. and the pressure is 45-55 Pa; most preferably, the heating temperature of the two-stage molecular distillation is 100° C. and the pressure is 50 Pa.
  • the method further includes the step of preprocessing the discarded cigarette butts;
  • the specific operation of the pretreatment is: tearing off the tipping paper of the discarded cigarette butts, removing the cigarette paper and the remaining shredded tobacco, collecting the fiber tow, and cutting the tow into small sections less than 1 cm in length.
  • the present invention also provides a tar extract prepared by the method.
  • the present invention also provides the application of the tar extract in the preparation of spices, and the tar extract is applied to the spices as a fragrance ingredient.
  • the present invention also provides the application of the tar extract in the preparation of cigarettes.
  • the tar extract is added to the cigarette auxiliary material or the reconstituted tobacco cut tobacco, and the added amount of the tar extract is 2 to 5% of the weight of the cigarette;
  • the cigarette is a low-end traditional cigarette.
  • the present invention uses subcritical extraction and molecular distillation to separate the tar extract, which removes harmful substances in tar and retains its aroma components; when applied to cigarettes, the aroma, smoke and taste characteristics of cigarettes are improved. Broaden the scope of application and usage of low-grade tobacco in middle and low-end cigarettes to provide an effective way.
  • the present invention obtains a tar extract with a higher extraction rate from the cigarette butt.
  • the present invention uses discarded cigarette butts as raw materials, which can not only prevent the cigarette butts from polluting the environment, but also utilize the by-product tar after cigarette burning.
  • the raw materials and equipment used can be purchased from the market or commonly used in the field.
  • Example 1 Using waste cigarette butts to extract tar extracts with aromatizing properties
  • a method for preparing a tar extract with aroma-generating properties by using waste cigarette butts including the following steps:
  • Pretreatment of discarded cigarette butts tear off the tipping paper of discarded cigarette butts, remove remaining shredded tobacco and cigarette paper, collect fiber tows, and cut the tows into small sections less than 1cm in length;
  • the concentrated extract is subjected to two-stage molecular distillation.
  • the heating temperature of the first-stage molecular distillation is 60°C, the pressure is 150Pa, the feeding speed is 400mL/h, and the scraping speed is 250rpm; the heating temperature of the second-stage molecular distillation is 100°C, pressure of 50 Pa, feed rate of 400 mL/h, and film scraping speed of 250 rpm; combining the light components of primary and secondary molecular distillation to obtain the tar extract.
  • the tar extract obtained was detected by GC/MS, and the obtained components were furfural, furfuryl alcohol, ethylene glycol diacetate, 1-(1,3-dioxolane-2-yl)acetone, 4-cyclopentene -1,3-dione, methylcyclopentenolone, nicotine, 2(5H)-furanone, 5-methylfuran aldehyde, 3-methyl-2-cyclopenten-1-one, methyl Cyclopentenolone, benzyl alcohol, 2,3-dimethyl-2-cyclopentenone, ethylcyclopentenolone, 5-hydroxymethylfurfural, vanillin, macrostigmine A, 2,4,4-Trimethylpentane-1,3-diylbis(2-methylpropionate), farnesol, phthalate-1-butyl-2-isobutyl ester, east Scopolactone, tributyl prop-1-ene-1,2,3-tricarboxylic acid ester.
  • Heating program 80°C(1min)2°C/min ⁇ 280°C(10min)
  • the cigarette tar extract prepared in Example 1 was added to the cigarette filter at a ratio of 2% of the weight of the cigarette to prepare a cigarette sample A with tar aroma components added.
  • the cigarette tar extract prepared in Example 1 was added to the shredded tobacco at a ratio of 2% of the weight of the cigarette to prepare a cigarette sample B with tar aroma components added.
  • the cigarette tar extract prepared in Example 1 was added to the shredded tobacco at a proportion of 3% of the weight of the cigarette to prepare a cigarette sample C with tar aroma components added.
  • the smoke characteristics, aroma characteristics and taste characteristics of cigarettes are improved to varying degrees.
  • the aroma quality and aroma of cigarettes The amount is obviously better, and the impurity is reduced; the concentration of smoke is increased, the strength is increased, the fineness and the agglomeration are improved; the irritation is reduced, the dryness is reduced, and the sweetness is increased.
  • the sensory quality of cigarettes can be effectively improved, and an effective way is provided for broadening the use range and usage amount of low-grade tobacco leaves in middle and low-end cigarettes.
  • a method for preparing a tar extract with aroma-generating properties by using waste cigarette butts including the following steps:
  • Pretreatment of discarded cigarette butts tear off the tipping paper of discarded cigarette butts, remove remaining shredded tobacco and cigarette paper, collect fiber tows, and cut the tows into small sections less than 1cm in length;
  • the concentrated extract is subjected to two-stage molecular distillation.
  • the heating temperature of the first-stage molecular distillation is 50°C, the pressure is 200Pa, the feed rate is 600mL/h, and the scraping speed is 300rpm; the heating temperature of the second-stage molecular distillation is At 90°C, the pressure is 60 Pa, the feed rate is 600 mL/h, and the film scraping speed is 300 rpm; combining the first and second molecular distillation light components to obtain the tar extract.
  • a method for preparing a tar extract with aroma-generating properties by using waste cigarette butts including the following steps:
  • Pretreatment of discarded cigarette butts tear off the tipping paper of discarded cigarette butts, remove residual shredded tobacco and cigarette paper, collect fiber tows, and cut the tows into small sections less than 1cm in length;
  • the concentrated extract is subjected to two-stage molecular distillation.
  • the heating temperature of the first-stage molecular distillation is 80°C, the pressure is 100Pa, the feed rate is 300mL/h, and the scraping speed is 200rpm; the heating temperature of the second-stage molecular distillation is 110°C, pressure of 40 Pa, feed rate of 300 mL/h, film scraping speed of 200 rpm; combining the first and second molecular distillation light components to obtain the tar extract.
  • step (4) the concentrated extract is subjected to first-level molecular distillation, the heating temperature of molecular distillation is 80 °C, the pressure is 100 Pa, the feed rate is 300 mL/h, and the The membrane speed was 200 rpm, and the tar extract was obtained.
  • the rest are the same as the method steps in Example 5.
  • step (4) the concentrated extract is subjected to one-stage molecular distillation, the heating temperature of molecular distillation is 110 °C, the pressure is 40 Pa, the feed rate is 300 mL/h, and the The membrane speed was 200 rpm, and the tar extract was obtained.
  • the rest are the same as the method steps in Example 5.
  • the types and contents of the tar extracts prepared in Examples 4-7 of the present invention were determined.
  • the measurement results showed that the types and contents of the tar extracts prepared in Examples 4 to 5 were greater than those of the tar extracts prepared in Examples 6-7.
  • the tar extracts prepared in Examples 4 to 7 of the present invention were added to shredded tobacco at a ratio of 2% of the weight of the cigarette to obtain HnB sample 4#, prepared cigarette sample 5#, and cigarette sample 6# And cigarette sample 7#.
  • HnB sample 4# prepared cigarette sample 5#
  • cigarette sample 6# prepared cigarette sample 7#
  • 20 or more smokers were organized to refer to the sensory evaluation method of tobacco in-process products (YC/T415- 2011), sensory evaluation was performed on cigarette samples, and the evaluation results are shown in Table 4.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)

Abstract

一种利用废弃烟蒂制备具有致香特性的焦油提取物，包括以下步骤：(1)将废弃烟蒂加入萃取溶剂进行亚临界萃取，得到萃取液；(2)将萃取液真空抽滤，滤液经减压蒸馏后，得到浓缩浸膏；(3)将浓缩浸膏进行分子蒸馏，收集分子蒸馏轻组分，得到具有致香特性的焦油提取物。利用亚临界萃取和分子蒸馏分离制备焦油提取物，去除了焦油中的有害物质，保留其致香成分；应用到卷烟中，改善了卷烟的香气、烟气和口感特性，为拓宽低次烟叶在中低端卷烟中应用范围和使用量提供有效途径。通过优化亚临界萃取和分子蒸馏分离的条件，从烟蒂中得到提取率较高的焦油提取物。

Description

利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用 技术领域
本发明涉及利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用，属于烟草工艺的技术领域。
背景技术
烟蒂是卷烟消费后的副产物，主要由滤棒、残余烟丝、卷烟纸、水松纸等组成。我国是卷烟生产和消费大国，伴随每年消耗掉的大量卷烟，产生了很多的废弃烟蒂，随手丢弃，污染环境。废弃烟蒂中截留的焦油物质既含有酮类、呋喃类、吡嗪类等对感官质量起正面作用的致香成分，也含有能提升消费者生理满足感的烟碱，也含有胺类、醛类等对感官起明显负面作用的有害物质。因此，对废弃烟蒂中的焦油物质进行提取，制备具有一定性能或作用的提取物具有重要的意义。
亚临界萃取技术是在超临界之后发展起来的又一新型提取分离技术，利用亚临界流体作为萃取溶剂，在密闭、无氧、低压、低温条件下萃取，具有溶剂易回收无残留、萃取产物不易氧化、溶剂选择范围广、萃取压力低相应地反应设备要求也低等优势，日益引起关注，得到推广应用。
CN109959649A中公开了一种具有化学发光性质的卷烟焦油提取物，该卷烟焦油提取物的制备方法，包括如下步骤：将卷烟焦油加入试剂进行提取，得到卷烟焦油提取物。所述卷烟焦油可通过如下步骤制备得到：抽吸卷烟，对产生的烟气进行过滤，收集烟气粒相物，得到卷烟焦油。该专利中卷烟焦油提取物是在自然光条件下的敞开体系中通过超声波提取制得的，因此包含的发光物质性质稳定，对光照、氧气及温度等因素不敏感；该提取物对介质pH值的发光响应范围宽，在酸性、中性或碱性条件下都可以发生化学发光反应。该专利中卷烟焦油为烟气粒相物中的焦油，制备出的焦油提取物具有发光性质，不涉及对卷烟烟蒂中的焦油进行提取，获得焦油致香成分。
CN102559388A公开了一种烟草精油及其制备方法和在卷烟中的应用，其中烟草精油由以下方法制得：废次烟末→有机溶剂提取→精油粗提取物→通入水蒸汽→冷凝→油水分离→烟草精油。将本发明的烟草精油作为增香剂加入到卷烟烟丝中，可以增加烟草本香、提高卷烟香气质量、减少烟草刺激和杂气、柔和烟气。该专利以卷烟生产过程中产生的废次烟末为原料，废次烟末中不含焦油成分，不涉及到对卷烟烟蒂的提取工艺。
发明内容
本发明的目的在于提供一种利用废弃烟蒂制备具有致香特性的焦油提取物的方法。本发明以废弃烟蒂为原料，采用亚临界萃取和分子蒸馏分离获得具有致香特性的焦油提取物，将得到的焦油提取物应用到卷烟中，可以提高卷烟的香气。
本发明所采用的原料废弃烟蒂为人们消费卷烟后随手丢弃在烟灰缸中、路边等处的烟头，其原料来源广泛，成本低廉；采用的废弃烟蒂的颜色发黄；本发明选用颜色发黄的烟蒂，其含有的焦油含量较高。
一方面，本发明提供了一种利用废弃烟蒂制备具有致香特性的焦油提取物的方法，该方法包括以下步骤：
(1)将废弃烟蒂加入萃取溶剂进行亚临界萃取，得到萃取液；
(2)将萃取液真空抽滤，滤液经减压蒸馏后，得到浓缩浸膏；
(3)将浓缩浸膏进行分子蒸馏，收集分子蒸馏轻组分，得到具有致香特性的焦油提取物。
优选的，步骤(1)中，所述萃取溶剂为正丁烷、乙醇、石油醚、正己烷、丙酮、二氯甲烷、乙酸乙酯中的至少一种；
优选的，废弃烟蒂与萃取溶剂的比例为1g：5～80mL。
优选的，步骤(1)中，所述亚临界萃取的条件为：萃取压力0.6～1.6MPa，萃取温度20～60℃，萃取时间为10～120min，萃取次数1～3次。更优选的，萃取压力0.7～1.2MPa，萃取压力的下限值选自0.8MPa、0.9MPa、1.0MPa或 1.1MPa。萃取压力的上限值选自0.8MPa、0.9MPa、1.0MPa或1.1MPa。更优选的，萃取温度30～50℃，萃取温度的下限值选自35℃、40℃或45℃，萃取温度的上限值选自35℃、40℃或45℃。更优选的，萃取时间为50～100min，萃取时间的下限值选自60min、70min、80min或90min，萃取时间的上限值选自60min、70min、80min或90min。
优选的，步骤(2)中，所述减压蒸馏的温度为25～45℃，压力为0.06～0.08Mpa。
优选的，步骤(3)中，所述分子蒸馏为两级分子蒸馏，合并一级和二级分子蒸馏的轻组分；
优选的，一级分子蒸馏的加热温度为50～80℃，压力为100～200Pa，进料速度为300～600mL/h，刮膜速度为200～300rpm；更优选的，一级分子蒸馏的加热温度为60～70℃。更优选的，压力为110Pa～190Pa；压力的下限值选自120Pa、130Pa、140Pa、150Pa、160Pa、170Pa或180Pa，压力的上限值选自120Pa、130Pa、140Pa、150Pa、160Pa、170Pa或180Pa。
优选的，二级分子蒸馏的加热温度为90～110℃，压力为40～60Pa，进料速度为300～600mL/h，刮膜速度为200～300rpm。更优选的，二级分子蒸馏的加热温度为95～105℃，压力为45～55Pa；最优选的，二级分子蒸馏的加热温度为100℃，压力为50Pa。
优选的，所述方法还包括对废弃烟蒂进行预处理的步骤；
优选的，所述预处理的具体操作为：撕去废弃烟蒂的水松纸，去掉卷烟纸和残余烟丝，收集纤维丝束，并将丝束剪成小于1cm长的小段。
第二方面，本发明还提供了所述的方法制得的焦油提取物。
第三方面，本发明还提供了所述的焦油提取物在制备香料中的应用，所述焦油提取物作为致香成分应用到香料中。
第四方面，本发明还提供了所述的焦油提取物在制备卷烟中的应用。
优选的，将焦油提取物添加到卷烟辅材或卷烟再造烟丝中，焦油提取物的添加量为卷烟烟支重量的2～5％；
优选的，所述卷烟为中低端传统卷烟。
本发明的有益效果为：
(1)本发明利用亚临界萃取和分子蒸馏分离制备焦油提取物，去除了焦油中的有害物质，保留其致香成分；应用到卷烟中，改善了卷烟的香气、烟气和口感特性，为拓宽低次烟叶在中低端卷烟中应用范围和使用量提供有效途径。
(2)本发明通过优化亚临界萃取和分子蒸馏分离的条件，从烟蒂中得到提取率较高的焦油提取物。且本发明以废弃的烟蒂为原料，既可避免烟蒂污染环境，又可将卷烟燃吸后副产物焦油利用起来。
具体实施方式
下面结合具体实施例对本发明进行详细说明，以下实施例仅为方便本领域技术人员理解本发明技术方案，实现或使用本发明所做的说明，并不以此限定本发明的保护范围。
本发明中，如未指定，所采用的原料和设备等均可从市场购得或是本领域常用的。
实施例中的方法，如无特殊说明，均为本领域的常规方法。
实施例1利用废弃烟蒂提取具有致香特性的焦油提取物
一种利用废弃烟蒂制备具有致香特性的焦油提取物的方法，包括以下步骤：
(1)废弃烟蒂的预处理：撕去废弃烟蒂的水松纸，去掉残余烟丝和卷烟纸，收集纤维丝束，并将丝束剪成小于1cm长的小段；
(2)在亚临界萃取罐中放入20g处理后的废弃烟蒂，注入800mL正丁烷，进行亚临界萃取，萃取压力1.0MPa，萃取温度40℃，萃取时间为70min，萃取1次，得到萃取液；
(3)将萃取液真空抽滤后，滤液在30℃，0.07Mpa条件下减压蒸馏，得到浓缩浸膏；
(4)将浓缩浸膏进行两级分子蒸馏，一级分子蒸馏的加热温度为60℃，压力为150Pa，进料速度为400mL/h，刮膜速度为250rpm；二级分子蒸馏的加热温度为100℃，压力为50Pa，进料速度为400mL/h，刮膜速度为250rpm；合并一级、二级分子蒸馏轻组分，即为所得焦油提取物。
对所得焦油提取物进行GC/MS检测，得到的成分为糠醛、糠醇、乙二醇二乙酸酯、1-(1,3-二氧戊环-2-基)丙酮、4-环戊烯-1,3-二酮、甲基环戊烯醇酮、烟碱、2(5H)-呋喃酮、5-甲基呋喃醛、3-甲基-2-环戊烯-1-酮、甲基环戊烯醇酮、苯甲醇、2,3-二甲基-2-环戊烯酮、乙基环戊烯醇酮、5-羟甲基糠醛、香草醛、巨豆三烯酮A、2,4,4-三甲基戊烷-1,3-二基双(2-甲基丙酸酯)、金合欢醇、邻苯二甲酸-1-丁酯-2-异丁酯、东莨菪内酯、三丁基丙-1-烯-1,2,3-三羧酸酯。
其中，GC/MS条件：
HP6890-5973气质联用仪
(1)GC条件：
色谱柱：ULTRA2(50m×0.2mm i.d×0.33μm d.f.)
检测器：MS
载气，流量：He，0.6ml/min
进样口温度：290℃
升温程序：80℃(1min)2℃/min→280℃(10min)
分流比，进样量：1:10，2μl
(2)GC/MS条件：
GC条件：同上
传输线温度：230℃
离子源温度：230℃
电离能：70eV
质量数范围：30～350u
载气：He
MS谱图：NIST库
实施例2将焦油提取物应用到卷烟中
将实施例1制得的卷烟焦油提取物以卷烟烟支重量的2％的比例添加到卷烟滤嘴中，制备添加焦油致香成分的卷烟样品A。
将实施例1制得的卷烟焦油提取物以卷烟烟支重量的2％的比例添加到卷烟烟丝中，制备添加焦油致香成分的卷烟样品B。
将实施例1制得的卷烟焦油提取物以卷烟烟支重量的3％的比例添加到卷烟烟丝中，制备添加焦油致香成分的卷烟样品C。
将上述方案制成的卷烟样品及不添加焦油致香成分的卷烟在(20±1)℃、相对湿度(60±3)％的恒温恒湿环境下平衡24h后，组织10位及以上评吸人员参考烟草在制品感官评价方法(YC/T 415-2011)，对卷烟样品进行感官评价，评价结果如表1所示。
表1添加焦油特色香原料卷烟的特征感官评价结果
Figure PCTCN2020129090-appb-000001
如表1所示，与对照组相比，添加本发明实施例制得的焦油提取物后，卷烟的烟气特性、香气特性及口感特性均得到不同程度的改善，其中，卷烟香气质、香气量明显变好，杂气减少；烟气浓度增加，劲头增大，细腻程度和成团 性均有所改善；刺激性减弱、干燥感降低、回甜感增强。添加本发明实施例制得的焦油提取物后，可有效改善卷烟感官质量，为拓宽低次烟叶在中低端卷烟中的使用范围和使用量提供有效途径。
实施例3制备方法条件的选择
1、萃取压力的选择
称取20g处理后的废弃烟蒂，加入亚临界萃取罐中，然后在萃取罐中注入800mL的正丁烷，萃取温度设定40℃，分别在萃取压力为0.6MPa、0.8MPa、1.0MPa、1.2MPa下对废弃烟蒂进行亚临界提取，提取1次，提取70min，对比分析不同萃取压力对提取效果的影响，检测结果如表2所示。由表2可知，在1.0MPa下的提取效果最好。
表2不同萃取压力的提取效果(mg/g)
Figure PCTCN2020129090-appb-000002
Figure PCTCN2020129090-appb-000003
2、亚临界萃取温度的选择
称取20g处理后的废弃烟蒂，加入亚临界萃取罐中，然后在萃取罐中注入800mL的正丁烷，萃取压力设定为1.0MPa，分别在萃取温度为30℃、35℃、40℃、45℃下对废弃烟蒂进行亚临界提取，提取1次，提取70min，对比分析不同萃取温度对提取效果的影响，检测结果如表3所示。如表3所示，在40℃下的萃取效果最好。
表3不同亚临界萃取温度的提取效果(mg/g)
Figure PCTCN2020129090-appb-000004
Figure PCTCN2020129090-appb-000005
实施例4
一种利用废弃烟蒂制备具有致香特性的焦油提取物的方法，包括以下步骤：
(1)废弃烟蒂的预处理：撕去废弃烟蒂的水松纸，去掉残余烟丝和卷烟纸，收集纤维丝束，并将丝束剪成小于1cm长的小段；
(2)在亚临界萃取罐中放入20g处理后的废弃烟蒂，注入100mL石油醚进行亚临界萃取，萃取压力1.0MPa，萃取温度40℃，萃取时间为10min，萃取3次，得到萃取液；
(3)将萃取液真空抽滤后，滤液在25℃，0.08Mpa条件下减压蒸馏，得到浓缩浸膏；
(4)将浓缩浸膏进行两级分子蒸馏，一级分子蒸馏的加热温度为50℃，压力为200Pa，进料速度为600mL/h，刮膜速度为300rpm；二级分子蒸馏的加热温度为90℃，压力为60Pa，进料速度为600mL/h，刮膜速度为300rpm；合并一级、二级分子蒸馏轻组分，即为所得焦油提取物。
实施例5
一种利用废弃烟蒂制备具有致香特性的焦油提取物的方法，包括以下步骤：
(1)废弃烟蒂的预处理：撕去废弃烟蒂的水松纸，去掉残余烟丝和卷烟 纸，收集纤维丝束，并将丝束剪成小于1cm长的小段；
(2)在亚临界萃取罐中放入20g处理后的废弃烟蒂，注入1.6L无水乙醇，进行亚临界萃取，萃取压力1.0MPa，萃取温度40℃，萃取时间为120min，萃取1次，得到萃取液；
(3)将萃取液真空抽滤后，滤液在45℃，0.06Mpa条件下减压蒸馏，得到浓缩浸膏；
(4)将浓缩浸膏进行两级分子蒸馏，一级分子蒸馏的加热温度为80℃，压力为100Pa，进料速度为300mL/h，刮膜速度为200rpm；二级分子蒸馏的加热温度为110℃，压力为40Pa，进料速度为300mL/h，刮膜速度为200rpm；合并一级、二级分子蒸馏轻组分，即为所得焦油提取物。
实施例6
该实施例6与实施例5的不同之处在于：步骤(4)将浓缩浸膏进行一级分子蒸馏，分子蒸馏的加热温度为80℃，压力为100Pa，进料速度为300mL/h，刮膜速度为200rpm，得到焦油提取物。其余与实施例5中方法步骤相同。
实施例7
该实施例7与实施例5的不同之处在于：步骤(4)将浓缩浸膏进行一级分子蒸馏，分子蒸馏的加热温度为110℃，压力为40Pa，进料速度为300mL/h，刮膜速度为200rpm，得到焦油提取物。其余与实施例5中方法步骤相同。
对本发明实施例4～7制得的焦油提取物的种类和含量进行测定，测定结果表明实施例4～5制得的焦油提取物的种类和含量大于实施例6～7制得的焦油提取物的种类和含量。
将本发明实施例4～7制得的焦油提取物，分别以以卷烟烟支重量的2％的比例添加到卷烟烟丝中，制得HnB样品4#、制备卷烟样品5#、卷烟样品6#和卷烟样品7#。将卷烟样品在(20±1)℃、相对湿度(60±3)％的恒温恒湿环境下平衡24h后，组织20位及以上评吸人员参考烟草在制品感官评价方法(YC/T 415-2011)，对卷烟样品进行感官评价，评价结果如表4所示。
表4感官评价结果
Figure PCTCN2020129090-appb-000006
由表4的结果可知，本发明实施例制得的焦油提取物添加到卷烟后，在卷烟香气特性、烟气特性和口感特性均有不同程度的改善，能可有效改善卷烟感官质量，为拓宽低次烟叶在中低端卷烟中的使用范围和使用量提供有效途径。
以上所述，仅为本申请的实施例而已，本申请的保护范围并不受这些具体实施例的限制，而是由本申请的权利要求书来确定。对于本领域技术人员来说，本申请可以有各种更改和变化。凡在本申请的技术思想和原理之内所作的任何修改、等同替换、改进等，均应包含在本申请的保护范围之内。

Claims (10)

  1. 一种利用废弃烟蒂制备具有致香特性的焦油提取物，其特征在于，该方法包括以下步骤：
    (1)将废弃烟蒂加入萃取溶剂进行亚临界萃取，得到萃取液；
    (2)将萃取液真空抽滤，滤液经减压蒸馏后，得到浓缩浸膏；
    (3)将浓缩浸膏进行分子蒸馏，收集分子蒸馏轻组分，得到具有致香特性的焦油提取物。
  2. 根据权利要求1所述的方法，其特征在于，步骤(1)中，所述萃取溶剂为正丁烷、乙醇、石油醚、正己烷、丙酮、二氯甲烷、乙酸乙酯中的至少一种；
    优选的，废弃烟蒂与萃取溶剂的比例为1g：5～80mL。
  3. 根据权利要求1所述的制备方法，其特征在于，步骤(1)中，所述亚临界萃取的条件为：萃取压力为0.6～1.6MPa，萃取温度为20～60℃，萃取时间为10～120min，萃取次数1～3次。
  4. 根据权利要求1所述的制备方法，其特征在于，步骤(2)中，所述减压蒸馏的温度为25～45℃，压力为0.06～0.08Mpa。
  5. 根据权利要求1所述的制备方法，其特征在于，步骤(3)中，所述分子蒸馏为两级分子蒸馏，合并一级和二级分子蒸馏的轻组分；
    优选的，一级分子蒸馏的加热温度为50～80℃，压力为100～200Pa，进料速度为300～600mL/h，刮膜速度为200～300rpm；
    优选的，二级分子蒸馏的加热温度为90～110℃，压力为40～60Pa，进料速度为300～600mL/h，刮膜速度为200～300rpm。
  6. 根据权利要求1所述的制备方法，其特征在于，所述方法还包括对废弃烟蒂进行预处理的步骤；
    优选的，所述预处理的具体操作为：撕去废弃烟蒂的水松纸，去掉卷烟纸和残余烟丝，收集纤维丝束，并将丝束剪成小于1cm长的小段。
  7. 权利要求1～6任一项所述的方法制得的焦油提取物。
  8. 权利要求7所述的焦油提取物在制备香料中的应用，其特征在于，所述焦油提取物作为致香成分应用到香料中。
  9. 权利要求7所述的焦油提取物在制备卷烟中的应用。
  10. 根据权利要求9所述的应用，其特征在于，将焦油提取物添加到卷烟辅材或卷烟再造烟丝中，焦油提取物的添加量为卷烟烟支重量的2～5％；
    优选的，所述卷烟为中低端传统卷烟。
PCT/CN2020/129090 2019-11-27 2020-11-16 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用 WO2021104082A1 (zh)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP20891974.6A EP4059358B1 (en) 2019-11-27 2020-11-16 Method for preparing tar extract having aromatic characteristics by using discarded cigarette butt, and use thereof in cigarette
US17/780,543 US11839232B2 (en) 2019-11-27 2020-11-16 Method for preparing tar extract having aromatic characteristics by using discarded cigarette butt, and use thereof in cigarette
JP2022531435A JP7340104B2 (ja) 2019-11-27 2020-11-16 廃棄吸い殻を用いて賦香特性を有するタール抽出物を製造する方法及び巻きタバコにおけるその使用
KR1020227021024A KR102614469B1 (ko) 2019-11-27 2020-11-16 폐기 담배 꽁초를 사용하여 향기 발생 특성이 있는 타르 추출물을 제조하는 방법 및 궐련에서 이의 응용

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201911179288.2A CN111035051B (zh) 2019-11-27 2019-11-27 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用
CN201911179288.2 2019-11-27

Publications (1)

Publication Number Publication Date
WO2021104082A1 true WO2021104082A1 (zh) 2021-06-03

Family

ID=70233622

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2020/129090 WO2021104082A1 (zh) 2019-11-27 2020-11-16 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用

Country Status (6)

Country Link
US (1) US11839232B2 (zh)
EP (1) EP4059358B1 (zh)
JP (1) JP7340104B2 (zh)
KR (1) KR102614469B1 (zh)
CN (1) CN111035051B (zh)
WO (1) WO2021104082A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113969213A (zh) * 2021-07-30 2022-01-25 吉林烟草工业有限责任公司 一种菌菇香净油、其制备方法和一种卷烟

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111035051B (zh) * 2019-11-27 2021-04-27 内蒙古昆明卷烟有限责任公司 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102559388A (zh) 2012-02-27 2012-07-11 浙江中烟工业有限责任公司 一种烟草精油及其制备方法和在卷烟中的应用
US20150201669A1 (en) * 2014-01-17 2015-07-23 R.J. Reynolds Tobacco Company Process for producing flavorants and related materials
CN105146739A (zh) * 2015-07-28 2015-12-16 中国烟草总公司郑州烟草研究院 一种毛烟精油的制备方法及其应用
CN105779128A (zh) * 2016-03-30 2016-07-20 浙江中烟工业有限责任公司 一种感官舒适度好的卷烟产品
CN109111992A (zh) * 2018-08-28 2019-01-01 云南恒罡科技有限公司 一种亚临界分子蒸馏联用烟草净油制备的方法
CN109959649A (zh) 2017-12-26 2019-07-02 中国农业科学院烟草研究所 一种具有化学发光性质的卷烟焦油提取物及其化学发光体系
CN111035051A (zh) * 2019-11-27 2020-04-21 内蒙古昆明卷烟有限责任公司 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2770239A (en) * 1952-02-04 1956-11-13 Prats Jose Romero Process of treating tobacco
WO2007012980A1 (en) * 2005-06-01 2007-02-01 Philip Morris Products S.A. Tobacco with an increased level of natural tar dilutents
CN105105317A (zh) 2015-08-14 2015-12-02 贵州中烟工业有限责任公司 一种浓香型加热不燃烧的烟草制品及其制备方法
CN105861154A (zh) 2016-03-30 2016-08-17 浙江中烟工业有限责任公司 利用超临界萃取和分子蒸馏定向分离烟草中致香物质的方法及应用
CN105747266B (zh) * 2016-04-20 2021-05-28 贵州中烟工业有限责任公司 一种加热不燃烧烟草卷烟烟支的制备方法
KR101691952B1 (ko) 2016-06-01 2017-01-03 (주)동성판금플랜트 소화 기능을 갖는 재떨이
CN106263013B (zh) 2016-11-22 2018-07-06 河南中烟工业有限责任公司 一种高香气烟草提取物、制备方法及其应用
CN110236231B (zh) 2019-06-27 2021-12-17 河南中烟工业有限责任公司 一种微波裂解-分子蒸馏联用的电子烟油制备方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102559388A (zh) 2012-02-27 2012-07-11 浙江中烟工业有限责任公司 一种烟草精油及其制备方法和在卷烟中的应用
US20150201669A1 (en) * 2014-01-17 2015-07-23 R.J. Reynolds Tobacco Company Process for producing flavorants and related materials
CN105146739A (zh) * 2015-07-28 2015-12-16 中国烟草总公司郑州烟草研究院 一种毛烟精油的制备方法及其应用
CN105779128A (zh) * 2016-03-30 2016-07-20 浙江中烟工业有限责任公司 一种感官舒适度好的卷烟产品
CN109959649A (zh) 2017-12-26 2019-07-02 中国农业科学院烟草研究所 一种具有化学发光性质的卷烟焦油提取物及其化学发光体系
CN109111992A (zh) * 2018-08-28 2019-01-01 云南恒罡科技有限公司 一种亚临界分子蒸馏联用烟草净油制备的方法
CN111035051A (zh) * 2019-11-27 2020-04-21 内蒙古昆明卷烟有限责任公司 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HUANG DENGFENG: "Studies on Recycling and Use of the Cigarette Butts", CHINESE MASTER’S THESES FULL-TEXT DATABASE, ENGINEERING SCIENCE AND TECHNOLOGY I, 1 June 2012 (2012-06-01), XP055814492 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113969213A (zh) * 2021-07-30 2022-01-25 吉林烟草工业有限责任公司 一种菌菇香净油、其制备方法和一种卷烟

Also Published As

Publication number Publication date
EP4059358B1 (en) 2024-02-14
JP2022551673A (ja) 2022-12-12
JP7340104B2 (ja) 2023-09-06
CN111035051A (zh) 2020-04-21
CN111035051B (zh) 2021-04-27
EP4059358A1 (en) 2022-09-21
US20230132114A1 (en) 2023-04-27
US11839232B2 (en) 2023-12-12
KR102614469B1 (ko) 2023-12-14
EP4059358A4 (en) 2023-02-01
KR20220124691A (ko) 2022-09-14

Similar Documents

Publication Publication Date Title
WO2021104081A1 (zh) 一种卷烟烟蒂中焦油致香成分的提取方法及其在卷烟中的应用
EP4059360B1 (en) Method for preparing tar extract from discarded cigarette butts and application thereof in cigarettes
WO2021104082A1 (zh) 利用废弃烟蒂制备具有致香特性的焦油提取物的方法及其在卷烟中的应用
CN102559388A (zh) 一种烟草精油及其制备方法和在卷烟中的应用
CN105533793B (zh) 一种晒红烟烟草提取物的制备方法
CN111035056B (zh) 一种烟蒂焦油提取物的制备方法及其在卷烟中的应用
CN111035058B (zh) 一种废弃烟蒂中焦油提取物的制备方法及其在卷烟中的应用
CN111789283B (zh) 一种基于超临界co2萃取技术的烟梗多级利用方法
CN111035054B (zh) 从废弃烟蒂中制备具有致香特性的焦油提取物的方法及其在卷烟中的应用
CN109700068A (zh) 一种漂油法制备晒烟净油的方法及其应用
CN111035052B (zh) 具有致香特性的卷烟烟蒂焦油提取物的制备方法及其在卷烟中的应用
CN111713730B (zh) 一种烟用增香减害颗粒及其制备方法和应用
CN111035053A (zh) 烟蒂焦油中致香成分的提取方法及其在卷烟中的应用
CN116264909A (zh) 一种基于透析原理制备烟草热解产物的方法及烟草热解产物和应用
CN114983003A (zh) 一种烟草提取物的制备方法及其应用
CN116622441A (zh) 一种半干馏天然香料及其制备方法与它的用途
CN116019251A (zh) 一种烤烟烟香香基及其制备方法
CN116355695A (zh) 一种白肋烟精油、含白肋烟精油的组合物及其制备和应用
CN110959892A (zh) 一种浸泡高压低温反应制备烟丝功能香原料的方法
CN116042315A (zh) 一种黄姜花香料及其制备方法与其在烟草制品中的应用
CN113508919A (zh) 烟草提取物及其制备方法和应用

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20891974

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022531435

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2020891974

Country of ref document: EP

Effective date: 20220616

NENP Non-entry into the national phase

Ref country code: DE